Aryl N-alkyl-N-(pyridyl or pyrimidyl) carbamate

ABSTRACT

Carbamate derivatives represented by the general formula (I); ##STR1## wherein X is 2-naphthyl, 5-indanyl, 5,6,7,8-tetrahydro-2-naphthyl, 1,4-methano-1,2,3,4-tetrahydro-6-naphthyl, 1,4-ethano-1,2,3,4-tetrahydro-6-naphthyl, 2-quinolyl, or substituted phenyl, 
     Y is an oxygen atom or a sulfur atom, 
     Z is lower alkyl, 
     W is pyridyl or pyrimidyl which is unsubstituted or substituted; process for the preparation of such compounds; 
     and herbicides containing the same as an active ingredient.

DETAILED EXPLANATION OF THE INVENTION

The present invention concerns carbamate derivatives, process for the preparation of such compounds, and herbicides comprising the same as an active ingredient.

Hitherto, it has been well-known that arylthiocarbamate derivatives have antifungal activity as drugs and also that aryl N-arylcarbamate derivatives can be used as herbicides.

The present inventors found and reported earlier that some N-pyridylcarbamate derivatives have herbicidal activity. Furthermore, the present invention was completed by earnestly conducted investigation to develop N-pyridylcarbamate and N-pyrimidylcarbamate derivatives which exhibited sufficient herbicidal activity and high selectivity.

More especially, the present invention provides carbamate derivatives represented by the general formula (I) (hereinafter referred to as the compounds of the present invention): ##STR2## wherein X is 2-naphthyl, 5-indanyl, 5,6,7,8-tetrahydro-2-naphthyl, 1,4-methano-1,2,3,4-tetrahydro-6-naphthyl, 1,4-ethano-1,2,3,4-tetrahydro-6-naphthyl, 2-quinolyl, or substituted phenyl having one or more than one of the same or different substituents selected from the group of halogeno, lower alkyl, lower alkenyl, lower alkoxy, lower alkenyloxy, lower alkynyloxy, lower alkylthio, lower alkylamino, (hydroxy-lower alkyl, (lower alkoxy-lower alkyl, acyl, nitro, cyano, methylenedioxy, and halogenated lower alkyl,

Y is an oxygen atom or a sulfur atom,

Z is lower alkyl,

W is pyridyl substituted by one or two of the same substituents selected from the group of halogeno, lower alkyl, and lower alkylamino when X is 2-naphthyl but W is pyridyl or pyrimidyl which is unsubstituted or substituted by one or two of the same or different substituents selected from the group of halogeno, nitro, lower alkyl, lower alkoxy, lower alkylthio, and lower alkylamino when X is other than 2-naphthyl,

process for the preparation of such compounds, and herbicides containing the same as an active ingredient.

The herbicides containing the compounds of the present invention show extremely excellent herbicidal activity against barnyard grass as well as many general weeds in the flooded paddy field, and they are substantially harmless against transplanted rice plants. Therefore, these herbicides are suitable for use in the paddy field. In addition, the herbicides containing the compounds of the present invention were recognized to have an applicability to be used in the farmland from the observation that they showed excellent herbicidal selectivity between gramineous weeds and broadleaved crops in the soil treatment of the farmland.

The carbamate derivatives of the present invention represented by the general formula (I) can be prepared according to the following reaction equations (1) and (2): ##STR3## wherein X is 2-naphthyl, 5-indanyl, 5,6,7,8-tetrahydro-2-naphthyl, 1,4-methano-1,2,3,4-tetrahydro-6-naphthyl, 1,4-ethano-1,2,3,4-tetrahydro-6-naphthyl, 2-quinolyl, or substituted phenyl having one or more than one of the same or different substituents selected from the group of halogeno, lower alkyl, lower alkenyl, lower alkoxy, lower alkenyloxy, lower alkynyloxy, lower alkylthio, lower alkylamino, hydroxy, -lower alkyl, lower alkoxy, -lower alkyl, acyl, nitro, cyano, methylenedioxy, and halogenated lower alkyl,

Y is an oxygen atom or a sulfur atom,

Z is lower alkyl,

W is pyridyl substituted by one or two of the same substituents selected from the group of halogeno, lower alkyl, and lower alkylamino when X is 2-naphthyl but W is pyridyl or pyrimidyl which is unsubstituted or substituted by one or two of the same or different substituents selected from the group of halogeno, nitro, lower alkyl, lower alkoxy, lower alkylthio, and lower alkylamino when X is other than 2-naphthyl,

Hal is a halogen atom.

The above-stated reactions proceed in the presence of dehydrohalogenation agents and further in the presence or absence of reaction solvents usually at the reaction temperature ranging from 0° to 150° C. during the reaction time ranging from about few minutes to 48 hours.

As the dehydrohalogenation agents, alkali hydroxides such as sodium hydroxide, potassium hydroxide and the like; alkali earth hydroxides such as calcium hydroxide and the like; alkali carbonates such as sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate and the like; metal hydrides such as sodium hydride and the like; and tertiary amines such as triethylamine, N,N-dimethylaniline, pyridine and the like can be exemplified. The starting amine derivatives can be used as the dehydrohalogenation agents in the reaction shown by the equation (2).

As the reaction solvents, water; alcohols such as methanol, ethanol, isopropanol and the like; ketones such as acetone, methyl ethyl ketone and the like; aromatic hydrocarbons such as benzene, toluene, xylene, and the like; ethers such as ethyl ether, tetrahydrofuran, dioxane and the like; halogenated hydrocarbons such as chlorobenzene; chloroform, carbon tetrachloride, dichloroethane and the like; and polar solvents such as dimethylformamide, dimethylsulfoxide and the like can be used.

Typical procedures for the preparation of the compounds of the present invention are explained in detail herein-below.

EXAMPLES EXAMPLE 1 Preparation of 4-isopropylphenyl N-(6-methoxy-2-pyridyl)-N-methylcarbamate (Compound No. 59)

A mixture of 2.01 g of N-(6-methoxy-2-pyridyl)-N-methylcarbamoylchloride, 1.36 g of 4-isopropylphenol, and 1.38 g of anhydrous potassium carbonate in 50 ml of methyl ethyl ketone was refluxed for 5 hours. After the reaction mixture was cooled to room temperature, it was poured into cold water and the product was extracted with benzene. The benzene solution, successively washed with water and brine, was dried over anhydrous magnesium sulfate. The residue obtained by the removal of benzene under reduced pressure was chromatographed through silica gel column using benzene as an eluent to give 2.56 g of pure 4-isopropylphenyl N-(6-methoxy-2-pyridyl)-N-methylcarbamate as solid in the yield of 85%. A part of the solid was recrystallized from hexane and crystals having melting point of 64° to 65° C. were obtained.

EXAMPLE 2 Preparation of O-4-chloro-3-methylphenyl N-methyl-N-(6-methyl-2-pyridyl)thiocarbamate (Compound No. 114)

A mixture of 2.01 g of N-methyl-N-(6-methyl-2-pyridyl)thiocarbamoylchloride, 1.43 g of 4-chloro-3-methylphenol, and 1.38 g of potassium carbonate in 50 ml of methyl ethyl ketone was refluxed for 48 hours. After the reaction mixture was cooled to room temperature, it was poured into cold water and the product was extracted with benzene. The benzene solution, successively washed with water and brine, was dried over anhydrous magnesium sulfate. The residue obtained by the removal of benzene under reduced pressure was chromatographed through silica gel column using hexane-ethyl acetate (3/1, V/V) as an eluent to give 1.07 g of pure O-4-chloro-3-methylphenyl N-methyl-N-(6-methyl-2-pyridyl)thiocarbamate as solid in the yield of 35%. A part of the solid was recrystallized from benzene-hexane and crystalls having melting point of 134° to 136° C. were obtained.

EXAMPLE 3 Preparation of 4-trifluoromethylphenyl N-(6-methoxy-2-pyridyl)-N-methylcarbamate (Compound No. 97)

To the mixture of 1.38 g of 2-methoxy-6-methylaminopyridine and 1.38 g of anhydrous potassium carbonate in 20 ml of acetone was added dropwise the solution of 2.25 g of 4-trifluoromethylphenyl chloroformate in 20 ml of acetone under stirring at room temperature. The mixture was stirred for 30 minutes and then was refluxed for 2 hours. After the reaction mixture was cooled to room temperature, it was poured into water and the product was extracted with benzene. The benzene solution, successively washed with water and brine, was dried over anhydrous magnesium sulfate. The residue obtained by the removal of benzene under reduced pressure was chromatographed through silica gel column using benzene as an eluent to give 2.02 g of pure 4-trifluoromethylphenyl N-(6-methoxy-2-pyridyl)-N-methylcarbamate as solid in the yield of 62%. A part of the solid was recrystallized from hexane and crystalls having melting point of 85° to 86° C. were obtained.

EXAMPLE 4 Preparation of O-3,4-dimethylphenyl N-methyl-N-(4-methyl-2 -pyridyl)thiocarbamate (Compound No. 115)

To the mixture of 1.22 g of 4-methyl-2-methylaminopyridine and 1.38 g of anhydrous potassium carbonate in 20 ml of acetone was added dropwise the solution of 2.01 g of O-3,4-dimethylphenyl chlorothioformate in 20 ml of acetone under stirring at room temperature. The mixture was stirred for 30 minutes and then was refluxed for 2 hours. After the reaction mixture was cooled to room temperature, it was poured into cold water and the product was extracted with benzene. The benzene solution, successively washed with water and brine, was dried over anhydrous magnesium sulfate. The residue obtained by the removal of benzene under reduced pressure was chromatographed through silica gel column using hexane-ethyl acetate (3/1, V/V) as an eluent to give 2.24 g of pure O-3,4-dimethylphenyl-methyl-N-(4-methyl-2-pyridyl)thiocarbamate as solid in the yield of 78%. A part of the solid was recrystallized from benzene-hexane and crystalls having melting point of 113° to 114° C. were obtained.

Typical examples of the compounds of the present invention having numbers of an identification are listed herein-below and those physical properties together with elemental analysis are shown in Table 1.

    __________________________________________________________________________     NO.                                                                               THE COMPOUNDS OF THE PRESENT INVENTION                                      __________________________________________________________________________     1. 2-Naphthyl N--methyl-N--(6-methyl-2-pyridyl)carbamate                       2. 2-Naphthyl N--methyl-N--(3-methyl-2-pyridyl)carbamate                       3. 0-2-Naphthyl N--methyl-N--(6-methyl-2-pyridyl)thiocarbamate                 4. 0-2-Naphthyl N--methyl-N--(4-methyl-2-pyridyl)thiocarbamate                 5. 0-5-Indanyl N--methyl-N--(6-methyl-2-pyridyl)thiocarbamate                  6. 0-5,6,7,8-Tetrahydro-2-naphthyl N--methyl-N--(6-methyl-2-pyridyl)thioca        rbamate                                                                     7. 0-5-Indanyl N--methyl-N--(5-methyl-2-pyridyl)thiocarbamate                  8. 0-5,6,7,8-Tetrahydro-2-naphthyl N--methyl-N--(5-methyl-2-pyridyl)thioca        rbamate                                                                     9. 0-5-Indanyl N--methyl-N--(4-methyl-2-pyridyl)thiocarbamate                  10.                                                                               0-5,6,7,8-Tetrahydro-2-naphthyl N--methyl-N--(4-methyl-2-pyridyl)thioca        rbamate                                                                        0-5-Indanyl N--methyl-N--(3-methyl-2-pyridyl)thiocarbamate                     0-5,6,7,8-Tetrahydro-2-naphthyl N--methyl-N--(3-methyl-2-pyridyl)thioca        rbamate                                                                        0-5-Indanyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate                    0-5,6,7,8-Tetrahydro-2-naphthyl N--(6-methoxy-2-pyridyl)-N--methylthioc        arbamate                                                                       0-1,4-Methano-1,2,3,4-tetrahydro-6-naphthyl N--(6-methoxy-2-pyridyl)-N-        -methylthiocarbamate                                                           5-Indanyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate                          5,6,7,8-Tetrahydro-2-naphthyl N--(6-methoxy-2-pyridyl)-N--methylcarbama        te                                                                             1,4-Methano-1,2,3,4-tetrahydro-6-naphthyl N--(6-methoxy-2-pyridyl)-N--m        ethylcarbamate                                                                 0-2-Naphthyl-N--methyl-N--(4,6-dimethyl-2-pyridyl)thiocarbamate             20.                                                                               0-5,6,7,8-Tetrahydro-2-naphthyl N--methyl-N--(4,6-dimethyl-2-pyridyl)th        iocarbamate                                                                    0-5-Indanyl N--methyl-N--(4,6-dimethyl-2-pyridyl)thiocarbamate                 0-2-Naphthyl N--(6-chloro-2-pyridyl)-N--methylthiocarbamate                    0-5,6,7,8-Tetrahydro-2-naphthyl N--(6-chloro-2-pyridyl)-N--methylthioca        rbamate                                                                        5,6,7,8-Tetrahydro-2-naphthyl N--(6-chloro-2-pyridyl)-N--methylcarbamat        e                                                                              0-5-Indanyl N--(6-chloro-2-pyridyl)-N--methylthiocarbamate                     0-5-Indanyl N--methyl-N--(2-pyridyl)thiocarbamate                              0-5,6,7,8-Tetrahydro-2-naphthyl N--methyl-N--(2-pyridyl)thiocarbamate          0-4-tert-Butylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate           0-4-tert-Butylphenyl N--methyl-N--(2-pyridyl)thiocarbamate                  30.                                                                               0-4-tert-Butylphenyl N--methyl-N--(6-methyl-2-pyridyl)thiocarbamate            0-4-tert-Butylphenyl N--methyl-N--(5-methyl-2-pyridyl)thiocarbamate            0-4-tert-Butylphenyl N--methyl-N--(4-methyl-2-pyridyl)thiocarbamate            0-4-tert-Butylphenyl N--methyl-N--(3-methyl-2-pyridyl)thiocarbamate            0-4-tert-Butylphenyl N--methyl-N--(4,6-dimethyl-2-pyridyl)thiocarbamate        4-tert-Butylphenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate                 0-4-tert-Pentylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate          0-5,6,7,8-Tetrahydro-2-naphthyl N--(6-bromo-2-pyridyl)-N--methylthiocar        bamate                                                                         0-1,4-Ethano-1,2,3,4-tetrahydro-6-naphthyl N--(6-methoxy-2-pyridyl)-N--        methyl-                                                                        thiocarbamate                                                                  0-3,4-Dimethylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate        40.                                                                               3,4-Dimethylphenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate                 0-5-Indanyl N--(4-ethyl-2-pyridyl)-N--methylthiocarbamate                      0-5,6,7,8-Tetrahydro-2-naphthyl N--(4-ethyl-2-pyridyl)-N--methylthiocar        bamate                                                                         0-2-Naphthyl N--(6-ethyl-2-pyridyl)-N--methylthiocarbamate                     0-5-Indanyl N--(6-ethyl-2-pyridyl)-N--methylthiocarbamate                      0-5,6,7,8-Tetrahydro-2-naphthyl N--(6-ethyl-2-pyridyl)-N--methylthiocar        bamate                                                                         0-4-tert-Butylphenyl N--(6-ethyl-2-pyridyl)-N--methylthiocarbamate             0-2-Naphthyl N--methyl-N--(5,6-dimethyl-2-pyridyl)thiocarbamate                0-5-Indanyl Naphthyl-N--(5,6-dimethyl-2-pyridyl)thiocarbamate                  0- 5,6,7,8-Tetrahydro-2-naphthyl N--methyl-N--(5,6-dimethyl-2-pyridyl)t        hiocarbamate                                                                50.                                                                               0-4-tert-Butylphenyl N--methyl-N--(5,6-dimethyl-2-pyridyl)thiocarbamate        0-3-tert-Butylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate           3-tert-Butylphenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate                 0-4-tert-Butylphenyl N--(6-bromo-2-pyridyl)-N--methylthiocarbamate             0-4-tert-Butylphenyl N--(6-chloro-2-pyridyl)-N--methylthiocarbamate            4-tert-Pentylphenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate                0-4-sec-Butylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate            4-sec-Butylphenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate                  0-4-Isopropylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate            4-Isopropylphenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate               60.                                                                               1,4-Ethano-1,2,3,4-tetrahydro-6-naphthyl N--(6-methoxy-2-pyridyl)-N--me        thylcarbamate                                                                  0-3-Methylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate               0-3-Ethylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate                0-4-Ethylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate                0-4-Bromophenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate                4-Bromophenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate                      0-4-Bromo-3,5-dimethylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarb        amate                                                                          0-4-Chloro-3,5-dimethylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocar        bamate                                                                         1,4-Methano-1,2,3,4-tetrahydro-6-naphthyl N--(6-bromo-2-pyridyl)-N--met        hylcarbamate                                                                   0-2-Naphthyl N--methyl-N--(6-dimethylamino-2-pyridyl)thiocarbamate          70.                                                                               0-5,6,7,8-Tetrahydro-2-naphthyl N--methyl-N--(6-dimethylamino-2-pyridyl        )thiocarbamate                                                                 0-5-Indanyl N--methyl-N--(6-dimethylamino-2-pyridyl)thiocarbamate              0-4-tert-Butylphenyl N--methyl-N--(6-dimethylamino-2-pyridyl)thiocarbam        ate                                                                            0-3-tert-Butylphenyl N--methyl-N--(2-pyridyl)thiocarbamate                     0-3-tert-Butylphenyl N--methyl-N--(3-methyl-2-pyridyl)thiocarbamate            0-3-tert-Butylphenyl N--methyl-N--(4-methyl-2-pyridyl)thiocarbamate            0-3-tert-Butylphenyl N--methyl-N--(5-methyl-2-pyridyl)thiocarbamate            0-3-tert-Butylphenyl N--methyl-N--(6-methyl-2-pyridyl)thiocarbamate            0-3-tert-Butylphenyl N--methyl-N--(4,6-dimethyl-2-pyridyl)thiocarbamate        0-3-tert-Butylphenyl N--methyl-N--(5,6-dimethyl-2-pyridyl)thiocarbamate     80.                                                                               0-3-tert-Butylphenyl N--methyl-N--(6-ethyl-2-pyridyl)thiocarbamate             4-tert-Butylphenyl N--methyl-N--(6-dimethylamino-2-pyridyl)carbamate           0-3,5-Dimethylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate           0-4-Chloro-3-methylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbama        te                                                                             4-Chloro-3-methylphenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate            0-4-(1,1,2-Trimethylpropyl)phenyl N--(6-methoxy-2-pyridyl)-N--methylthi        ocarbamate                                                                     0-4-Chlorophenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate               0-4-Ethyl-3-methylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamat        e                                                                              4-Ethyl-3-methylphenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate             0-4-Acetyl-3-methylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbama        te                                                                          90.                                                                               0-5-Isopropyl-2-methylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarb        amate                                                                          0-4-Isobutylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate             0-4-Isopropyl-3-methylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarb        amate                                                                          4-Isopropyl-3-methylphenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate         0-4-tert-Butyl-3-methylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocar        bamate                                                                         4-tert-Butyl-3-methylphenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate        0-4-Trifluoromethylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbama        te                                                                             4-Trifluoromethylphenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate            0-4-Nitrophenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate                0-3-Chloro-4-methylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbama        te                                                                          100.                                                                              3-Chloro-4-methylphenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate         101.                                                                              0-4-Bromo-3-methylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamat        e                                                                           102.                                                                              4-Bromo-3-methylphenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate          103.                                                                              0-5,6,7,8-Tetrahydro-2-naphthyl N--(6-chloro-4-pyrimidyl)-N--methylthio        carbamate                                                                   104.                                                                              0-4-tert-Butylphenyl N--(6-chloro-4-pyrimidyl)-N--methylthiocarbamate       105.                                                                              0-5,6,7,8-Tetrahydro-2-naphthyl N--(6-chloro-2-methylthio-4-pyrimidyl)-        N--methyl-                                                                     thiocarbamate                                                               106.                                                                              0-3-Trifluoromethylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbama        te                                                                          107.                                                                              3-Trifluoromethylphenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate         108.                                                                              0-3-Isopropylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate         109.                                                                              0-3-Chlorophenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate            110.                                                                              0-3-Bromophenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate             111.                                                                              3-Bromophenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate                   112.                                                                              1,4-Ethano-1,2,3,4-tetrahydro-6-naphthyl N--(6-bromo-2-pyridyl)-N--meth        ylcarbamate                                                                 113.                                                                              0-3,4-Dichlorophenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate        114.                                                                              0-4-Chloro-3-methylphenyl N--methyl-N--(6-methyl-2-pyridyl)thiocarbamat        e                                                                           115.                                                                              0-3,4-Dimethylphenyl N--methyl-N--(4-methyl-2-pyridyl)thiocarbamate         116.                                                                              0-2-Methylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate            117.                                                                              0-4-Methylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate            118.                                                                              4-Chloro-3-methoxyphenol N--(6-methoxy-2-pyridyl)-N--methylcarbamate        119.                                                                              0-4-Chloro-3-methoxyphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbam        ate                                                                         120.                                                                              3-Allyloxy-4-chlorophenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate       121.                                                                              0-3-Allyloxy-4-chlorophenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarba        mate                                                                        122.                                                                              4-Chloro-3-(2-propynyloxy)phenyl N--(6-methoxy-2-pyridyl)-N--methylcarb        amate                                                                       123.                                                                              4-Hydroxymethylphenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate           124.                                                                              4-Acetylphenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate                  125.                                                                              0-4-Isopropenylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate       126.                                                                              0-4-Cyanophenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate             127.                                                                              0-4-tert-Butylphenyl N--(2-chloro-4-pyrimidyl)-N--methylthiocarbamate       128.                                                                              0-4-tert-Butylphenyl N--methyl-N--(6-methylamino-5-nitro-2-pyridyl)thio        carbamate                                                                   129.                                                                              0-3-tert-Butylphenyl N--methyl-N--(6-methylamino-5-nitro-2-pyridyl)thio        carbamate                                                                   130.                                                                              0-5,6,7,8-Tetrahydro-2-naphthyl N--methyl N--(6-methylamino-5-nitro-2-p        yridyl)-                                                                       thiocarbamate                                                               131.                                                                              0-3-tert-Butylphenyl N--methyl-N--(6-dimethylamino-2-pyridyl)thiocarbam        ate                                                                         132.                                                                              0-4-tert-Butylphenyl N--methyl-N--(6-methylamino-2-pyridyl)thiocarbamat        e                                                                           133.                                                                              0-3-tert-Butylphenyl N--methyl-N--(6-methylamino-2-pyridyl)thiocarbamat        e                                                                           134.                                                                              3-Methoxyphenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate                 135.                                                                              0-3-Methoxyphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate           136.                                                                              4-Methoxyphenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate                 137.                                                                              0-4-Methoxyphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate           138.                                                                              3-Ethoxyphenyl-N--(6-methoxy-2-pyridyl)-N--methylcarbamate                  139.                                                                              0-3-Ethoxyphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate            140.                                                                              4-Ethoxyphenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate                  141.                                                                              0-4-Ethoxyphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate            142.                                                                              3-Butoxyphenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate                  143.                                                                              0-3-Butoxyphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate            144.                                                                              4-Butoxyphenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate                  145.                                                                              0-4-Butoxyphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate            146.                                                                              0-4-(1-Hydroxyethyl)phenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbam        ate                                                                         147.                                                                              0-3-tert-Butylphenyl N--(6-ethoxy-2-pyridyl)-N--methylthiocarbamate         148.                                                                              0-4-Methylthiophenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate        149.                                                                              0-3,4-Methylenedioxyphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbam        ate                                                                         150.                                                                              0-4-Chloro-3-methylphenyl N--methyl-N--(2-pyridyl)thiocarbamate             151.                                                                              0-4-Chloro-3-methylphenyl N--methyl-N--(5-methyl-2-pyridyl)thiocarbamat        e                                                                           152.                                                                              0-4-Chloro-3-methylphenyl N--methyl-N--(3-methyl-2-pyridyl)thiocarbamat        e                                                                           153.                                                                              0-4-Chloro-3-methylphenyl N--(6-ethyl-2-pyridyl)-N--methylthiocarbamate     154.                                                                              0-4-Chloro-3-methylphenyl N--methyl-N--(5,6-dimethyl-2-pyridyl)thiocarb        amate                                                                       155.                                                                              0-4-Chloro-3-methylphenyl N--methyl-N--(4,6-dimethyl-2-pyridyl)thiocarb        amate                                                                       156.                                                                              0-4-Chloro-3-methylphenyl N--(6-chloro-2-pyridyl)-N--methylthiocarbamat        e                                                                           157.                                                                              0-4-Chloro-3-methylphenyl N--methyl-N--(6-dimethylamino-2-pyridyl)thioc        arbamate                                                                    158.                                                                              0-4-Chloro-3-methylphenyl N--ethyl-N--(6-methoxy-2-pyridyl)thiocarbamat        e                                                                           159.                                                                              0-4-tert-Butylphenyl N--(6-chloro-2-pyridyl)-N--ethylthiocarbamate          160.                                                                              0-3-tert-Butylphenyl N--(6-chloro-2-pyridyl)-N--ethylthiocarbamate          161.                                                                              0-4-tert-Butylphenyl N--ethyl-N--(6-methoxy-2-pyridyl)thiocarbamate         162.                                                                              0-3-tert-Butylphenyl N--ethyl-N--(6-methoxy-2-pyridyl)thiocarbamate         163.                                                                              0-5,6,7,8-Tetrahydro-2-naphthyl N--ethyl-N--(6-methoxy-2-pyridyl)thioca        rbamate                                                                     164.                                                                              0-3-tert-Butylphenyl N--(6-chloro-2-pyridyl)-N--propylthiocarbamate         165.                                                                              0-4-tert-Butylphenyl N--(6-methoxy-2-pyridyl)-N--propylthiocarbamate        166.                                                                              0-3-tert-Butylphenyl N--(6-methoxy-2-pyridyl)-N--propylthiocarbamate        167.                                                                              0-5,6,7,8-Tetrahydro-2-naphthyl N--(6-methoxy-2-pyridyl)-N--propylthioc        arbamate                                                                    168.                                                                              0-4-tert-Butylphenyl N-- 13 isopropyl-N--(6-methoxy-2-pyridyl)thiocarba        mate                                                                        169.                                                                              0-3-tert-Butylphenyl N--isopropyl-N--(6-methoxy-2-pyridyl)thiocarbamate     170.                                                                              0-5,6,7,8-Tetrahydro-2-naphthyl N--isopropyl-N--(6-methoxy-2-pyridyl)th        iocarbamate                                                                 171.                                                                              4-Propylphenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate                  172.                                                                              0-4-Propylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate            173.                                                                              3-Methyl-4-nitrophenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate          174.                                                                              0-3-Methyl-4-nitrophenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamat        e                                                                           175.                                                                              0-3-Methyl-4-methylthiophenyl N--(6-methoxy-2-pyridyl)-N--methylthiocar        bamate                                                                      176.                                                                              0-4-Trifluoromethylphenyl N--methyl-N--(2-pyridyl)thiocarbamate             177.                                                                              0-4-Trifluoromethylphenyl N--methyl-N--(6-methyl-2-pyridyl)thiocarbamat        e                                                                           178.                                                                              0-4-Trifluoromethylphenyl N--methyl-N--(5-methyl-2-pyridyl)thiocarbamat        e                                                                           179.                                                                              0-4-Trifluoromethylphenyl N--methyl-N--(4-methyl-2-pyridyl)thiocarbamat        e                                                                           180.                                                                              0-4-Trifluoromethylphenyl N--methyl-N--(3-methyl-2-pyridyl)thiocarbamat        e                                                                           181.                                                                              0-4-Trifluoromethylphenyl N--methyl-N--(5,6-dimethyl-2-pyridyl)thiocarb        amate                                                                       182.                                                                              0-4-Trifluoromethylphenyl N--methyl N--(4,6-dimethyl-2-pyridyl)thiocarb        amate                                                                       183.                                                                              0-4-Trifluoromethylphenyl N--(6-ethyl-2-pyridyl)-N--methylthiocarbamate     184.                                                                              0-4-Trifluoromethylphenyl N--(6-chloro-2-pyridyl)-N--methylthiocarbamat        e                                                                           185.                                                                              0-4-Trifluoromethylphenyl N--(6-bromo-2-pyridyl)-N--methylthiocarbamate     186.                                                                              0-4-Trifluoromethylphenyl N--methyl-N--(6-dimethylamino-2-pyridyl)thioc        arbamate                                                                    187.                                                                              0-4-Chloro-3-methylphenyl N--(6-bromo-2-pyridyl)-N--methylthiocarbamate        8                                                                           188.                                                                              0-3-Dimethylaminophenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate        4                                                                           189.                                                                              3-Dimethylaminophenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate           190.                                                                              4-Formylphenyl N--(6-methoxy-2-pyridyl)-N--methylcarbamate                  191.                                                                              0-4-(1-Bromoethyl)phenyl N--(6-methoxy-2-pyridyl)-N--                          methylthiocarbamate                                                         192.                                                                              0-4-Trifluoromethylphenyl N--ethyl-N--(6-methoxy-2-pyridyl)thiocarbamat        e                                                                           193.                                                                              0-4-Ethylphenyl N--ethyl-N--(6-methoxy-2-pyridyl)thiocarbamate              194.                                                                              0-4-Isopropylphenyl N--ethyl-N--(6-methoxy-2-pyridyl)thiocarbamate          195.                                                                              0-5-Indanyl N--ethyl-N--(6-methoxy-2-pyridyl)thiocarbamate                  196.                                                                              0-1,4-Methano-1,2,3,4-tetrahydro-6-naphthyl N--ethyl-N--(6-methoxy-2-py        ridyl)-                                                                        thiocarbamate                                                               197.                                                                              0-5,6,7,8-Tetrahydro-2-naphthyl N--ethyl-N--(2-pyridyl)thiocarbamate        198.                                                                              0-5,6,7,8-Tetrahydro-2-naphthyl N--ethyl-N--(6-methyl-2-pyridyl)thiocar        bamate                                                                      199.                                                                              0-5,6,7,8-Tetrahydro-2-naphthyl N--(6-bromo-2-pyridyl)-N--ethylthiocarb        amate                                                                       200.                                                                              5,6,7,8-Tetrahydro-2-naphthyl N--ethyl-N--(6-methoxy-2-pyridyl)carbamat        e                                                                           201.                                                                              0-4-Methoxymethylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate     202.                                                                              0-4-Butylphenyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate             203.                                                                              0-2-Quinolyl N--(6-methoxy-2-pyridyl)-N--methylthiocarbamate                __________________________________________________________________________

                                      TABLE 1                                      __________________________________________________________________________     No. of                                                                         the                                                                            compound                                                                             Physical properties and elemental analysis                               of the                           Elemental analysis (%)                        present                                                                              Melting                    Found value                                   inven-                                                                               point                                                                               IR spectrum                                                                           NMR spectrum   (Calculated value)                            tion  (°C.)                                                                        (cm.sup.-1, KBr)                                                                      (δ = ppm, CDCl.sub.3)                                                                   C   H   N                                     __________________________________________________________________________     1     91-  1335   2.46(3H, s)    73.89                                                                              5.39                                                                               9.71                                        92.5 1415   3.57(3H, s)    (73.95)                                                                            (5.51)                                                                             (9.58)                                           1460   6.73-7.93(10H, m)                                                       1575                                                                           1715                                                                2     92.5-                                                                               1350   2.36(3H, s)    73.71                                                                              5.61                                                                               9.19                                        94.5 1450   3.40(3H, s)    (73.95)                                                                            (5.51)                                                                             (9.58)                                           1570   6.97-7.90(9H, m)                                                        1715   8.32(1H, d)                                                  3     149.5-                                                                              1300   2.52(3H, s)    69.89                                                                              5.19                                                                               8.89                                        150.5                                                                               1365   3.73(3H, s)    (70.10)                                                                            (5.22)                                                                             (9.08)                                           1440   6.90-7.96(10H, m)                                                       1595                                                                4     107- 1295   2.31(3H, s)    69.91                                                                              5.05                                                                               9.21                                        108.5                                                                               1380   3.73(3H, s)    (70.10)                                                                            (5.22)                                                                             (9.08)                                           1405   6.97(1H, d)                                                             1480   7.10-7.95(8H, m)                                                        1600   8.36(1H, d)                                                  5     140- 1300   2.02(2H, mc)   68.77                                                                              6.10                                                                               9.45                                        141  1370   2.52(3H, s)    (68.43)                                                                            (6.06)                                                                             (9.39)                                           1440   2.85(4H, t)                                                             1480   3.71(3H, s)                                                             1595   6.65-7.80(6H, m)                                             6     137.5-                                                                              1300   1.72(4H, mc)   69.50                                                                              6.51                                                                               9.06                                        139  1375   2.51(3H, s)    (69.28)                                                                            (6.46)                                                                             (8.98)                                           1440   2.70(4H, mc)                                                            1480   3.70(3H, s)                                                             1595   6.63-7.76(6H, m)                                             7     123- 1300   2.03(2H, mc) 8.30(1H, bs)                                                                     68.40                                                                              6.14                                                                               9.48                                        124.5                                                                               1380   2.30(3H, s)    (68.43)                                                                            (6.08)                                                                             (9.39)                                           1440   2.85(4H, t)                                                             1480   3.70(3H, s)                                                             1575   6.65-7.66(5H, m)                                             8     118.5-                                                                              1300   1.72(4H, mc) 8.30(1H, bs)                                                                     69.41                                                                              6.43                                                                               8.93                                        119  1380   2.30(3H, s)    (69.28)                                                                            (6.46)                                                                             (8.98)                                           1445   2.70(4H, mc)                                                            1480   3.68(3H, s)                                                             1575   6.65-7.70(5H, m)                                             9     93.5-                                                                               1300   2.03(2H, mc) 8.34(1H, d)                                                                      68.76                                                                              6.09                                                                               9.42                                        95   1380   2.33(3H, s)    (68.43)                                                                            (6.08)                                                                             (9.39)                                           1405   2.86(4H, t)                                                             1480   3.70(3H, s)                                                             1605   6.66-7.37(5H, m)                                             10    98-  1300 1605                                                                             1.72(4H, mc) 8.32(1H, d)                                                                      68.97                                                                              6.51                                                                               9.02                                        99.5 1375   2.32(3H, s)    (69.28)                                                                            (6.46)                                                                             (8.98)                                           1400   2.70(4H, mc)                                                            1440   3.68(3H, s)                                                             1480   6.62-7.38(5H, m)                                             11    113- 1290   2.00(2H, mc) 6.60-7.34(4H, m)                                                                 68.81                                                                              6.11                                                                               9.31                                        114  1380   2.33(3H, s) 7.57(1H, d)                                                                       (68.43)                                                                            (6.08)                                                                             (9.39)                                           1415   2.81(4H, t) 8.35(1H, d)                                                 1480   3.53(0.7H, s)                                                           1575   3.62(2.3H, s)                                                12    92.5-                                                                               1285   1.73(4H, mc) 6.55-7.33(4H, m)                                                                 69.36                                                                              6.51                                                                               8.93                                        93.5 1380   2.33(3H, s) 7.57(1H, d)                                                                       (69.28)                                                                            (6.46)                                                                             (8.98)                                           1420   2.68(4H, mc) 8.35(1H, d)                                                1490   3.53(0.7H, s)                                                           1575   3.63(2.3H, s)                                                13    95-  1370   2.04(2H, p)    65.25                                                                              5.74                                                                               9.10                                        96   1420   2.87(4H, t)    (64.95)                                                                            (5.77)                                                                             (8.91)                                           1465   3.73(3H, s)                                                             1605   3.89(3H, s)                                                                    6.46-7.75(6H, m)                                             14    98.5-                                                                               1375   1.77(4H, mc)   65.69                                                                              6.12                                                                               8.77                                        99.5 1430   2.67(4H, mc)   (65.83)                                                                            (6.14)                                                                             (8.53)                                           1470   3.70(3H, s)                                                             1605   3.86(3H, s)                                                                    6.45-7.73(6H, m)                                             15    91-  1365   1.52(6H, mc)   67.14                                                                              5.90                                                                               8.11                                        93   1410   3.39(2H, s)    (67.03)                                                                            (5.92)                                                                             (8.23)                                           1450   3.76(3H, s)                                                             1600   3.95(3H, s)                                                                    6.57-7.80(6H, m)                                             16    97-  1350   2.07(2H, p)    68.63                                                                              6.02                                                                               9.24                                        98.5 1410   2.85(4H, t)    (68.44)                                                                            (6.08)                                                                             (9.39)                                           1460   3.55(3H, s)                                                             1585   3.88(3H, s)                                                             1715   6.45-7.75(6H, m)                                             17    94-  1345   1.80(4H, mc)   68.95                                                                              6.51                                                                               9.18                                        94.5 1410   2.80(4H, mc)   (67.21)                                                                            (6.45)                                                                             (8.97)                                           1465   3.63(3H, s)                                                             1585   3.98(3H, s)                                                             1718   6.45-7.80(6H, m)                                             18    60.5-                                                                               1340   1.48(6H, mc)   70.69                                                                              6.22                                                                               8.47                                        62   1410   3.35(2H, s)    (70.35)                                                                            (6.21)                                                                             (8.63)                                           1460   3.59(3H, s)                                                             1580   3.93(3H, s)                                                             1718   6.35-7.75(6H, m)                                             19    117- 1320   2.23(3H, s)    70.91                                                                              5.81                                                                               8.55                                        119  1365   2.47(3H, s)    (70.77)                                                                            (5.62)                                                                             (8.68)                                           1405   3.72(3H, s)                                                             1440   6.83(1H, s)                                                             1610   6.99-7.95(8H, m)                                             20    116- 1320   1.73(4H, mc) 6.65-7.20(5H, m)                                                                 69.56                                                                              6.82                                                                               8.65                                        117.5                                                                               1370   2.27(3H, s)    (69.90)                                                                            (6.79)                                                                             (8.58)                                           1470   2.46(3H, s)                                                             1610   2.70(4H, mc)                                                                   3.67(3H, s)                                                  21    128- 1320   2.03(2H, mc) 6.68-7.33(5H, m)                                                                 69.14                                                                              6.41                                                                               9.04                                        129  1375   2.28(3H, s)    (69.28)                                                                            (6.46)                                                                             (8.98)                                           1480   2.48(3H, s)                                                             1610   2.86(4H, t)                                                                    3.67(3H, s)                                                  22    155.5-                                                                              1320   3.73(3H, s)    62.38                                                                              4.03                                                                               8.73                                        156.5                                                                               1365   7.07-7.96(10H, m)                                                                             (62.09)                                                                            (3.98)                                                                             (8.51)                                           1430                                                                           1480                                                                           1580                                                                23    126- 1300   1.69(4H, mc)   61.47                                                                              5.28                                                                               8.34                                        127.5                                                                               1360   2.67(4H, mc)   (61.34)                                                                            (5.15)                                                                             (8.42)                                           1420   3.68(3H, s)                                                             1460   6.60-7.80(6H, m)                                                        1575                                                                24    70-  1350   1.75(4H, mc)   64.68                                                                              5.50                                                                               8.88                                        71   1410   2.74(4H, mc)   (64.46)                                                                            (5.41)                                                                             (8.84)                                           1470   3.58(3H, s)                                                             1580   6.60-7.90(6H, m)                                                        1720                                                                25    124- 1295   2.02(2H, p)    60.55                                                                              4.80                                                                               8.85                                        125  1365   2.84(4H, t)    (60.28)                                                                            (4.74)                                                                             (8.79)                                           1420   3.71(3H, s)                                                             1470   6.50-7.80(6H, m)                                                        1565                                                                26    94-  1305   2.03(2H, p)    67.36                                                                              5.76                                                                               9.95                                        96   1380   2.86(4H, t)    (67.58)                                                                            (5.67)                                                                             (9.85)                                           1425   3.73(3H, s)                                                             1470   6.67-7.90(6H, m)                                                        1585   8.35-8.65(1H, m)                                             27    119.5-                                                                              1300   1.71(4H, mc)   68.29                                                                              6.06                                                                               9.35                                        121  1370   2.70(4H, mc)   (68.43)                                                                            (6.08)                                                                             (9.39)                                           1420   3.72(3H, s)                                                             1465   6.65-7.87(6H, m)                                                        1585   8.32-8.60(1H, m)                                             28    87-  1320   1.28(9H, s)    65.55                                                                              6.63                                                                               8.55                                        88   1370   3.71(3H, s)    (65.43)                                                                            (6.71)                                                                             (8.48)                                           1420   3.90(3H, s)                                                             1460   6.50-7.76(7H, m)                                                        1595                                                                29    100.5-                                                                              1300   1.28(9H, s)    67.84                                                                              6.75                                                                               9.28                                        101  1375   3.73(3H, s)    (67.98)                                                                            (6.71)                                                                             (9.33)                                           1430   6.80-7.85(7H, m)                                                        1465   8.47(1H, d)                                                             1585                                                                30    127- 1300   1.27(9H, s)    68.87                                                                              7.13                                                                               8.86                                        128.5                                                                               1370   2.52(3H, s)    (68.76)                                                                            (7.05)                                                                             (8.91)                                           1460   3.71(3H, s)                                                             1595   6.80-7.73(7H, m)                                             31    113- 1305   1.28(9H, s)    68.88                                                                              7.01                                                                               8.94                                        114  1380   2.32(3H, s)    (68.76)                                                                            (7.05)                                                                             (8.91)                                           1480   3.70(3H, s)                                                             1580   6.78-7.65(6H, m)                                                               8.30(1H, bs)                                                 32    107- 1290   1.28(9H, s)    69.08                                                                              7.03                                                                               8.89                                        108  1380   2.33(3H, s)    (68.76)                                                                            (7.05)                                                                             (8.91)                                           1400   3.69(3H, s)                                                             1480   6.80-7.48(6H, m)                                                        1605   8.30(1H, d)                                                  33    118.5-                                                                              1290   1.27(9H, s) 8.26-8.50(1H, m)                                                                  68.64                                                                              7.12                                                                               8.83                                        119  1375   2.34(3H, s)    (68.76)                                                                            (7.05)                                                                             (8.91)                                           1415   3.54(0.6H, s)                                                           1475   3.63(2.4H, s)                                                           1570   6.75-7.73(6H, m)                                             34    126.5-                                                                              1320   1.28(9H, s)    69.55                                                                              7.40                                                                               8.45                                        127.5                                                                               1380   2.28(3H, s)    (69.48)                                                                            (7.37)                                                                             (8.53)                                           1405   2.47(3H, s)                                                             1485   3.65(3H, s)                                                             1610   6.77-7.46(6H, m)                                             35    78-  1300 1710                                                                             1.33(9H, s)    69.11                                                                              7.09                                                                               8.83                                        80   1340   3.60(3H, s)    (68.77)                                                                            (7.05)                                                                             (8.91)                                           1405   3.93(3H, s)                                                             1460   6.36-7.73(7H, m)                                                        1575                                                                36    113- 1320   0.71(3H, t) 6.56-7.76(7H, m)                                                                  66.39                                                                              6.96                                                                               8.18                                        114.5                                                                               1365   1.31(6H, s)    (66.26)                                                                            (7.02)                                                                             (8.13)                                           1420   1.66(2H, q)                                                             1460   3.80(3H, s)                                                             1595   3.96(3H, s)                                                  37    132.5-                                                                              1290   1.75(4H, mc)   53.73                                                                              4.59                                                                               7.38                                        133.5                                                                               1360   2.74(4H, mc)   (54.12)                                                                            (4.54)                                                                             (7.42)                                           1415   3.71(3H, s)                                                             1460   6.60-7.70(6H, m)                                                        1565                                                                38    125- 1370   1.59(8H, mc)   67.47                                                                              6.30                                                                               7.75                                        126.5                                                                               1415   2.96(2H, s)    (67.78)                                                                            (6.25)                                                                             (7.90)                                           1455   3.76(3H, s)                                                             1600   3.93(3H, s)                                                                    6.50-7.70(6H, m)                                             39    111- 1320   2.22(6H, s)    63.35                                                                              6.07                                                                               9.04                                        112  1365   3.73(3H, s)    (63.55)                                                                            (6.00)                                                                             (9.26)                                           1410   3.90(3H, s)                                                             1455   6.45-7.23(5H, m)                                                        1595   7.55(1H, t)                                                  40    91-  1350   2.20(6H, s)    67.32                                                                              6.52                                                                               9.95                                        92   1410   3.56(3H, s)    (67.11)                                                                            (6.33)                                                                             (9.78)                                           1460   3.90(3H, s)                                                             1580   6.50(1H, d)                                                             1715   6.70-7.76(5H, m)                                             41    94-  1300   1.23(3H, t) 8.38(1H, d)                                                                       69.15                                                                              6.42                                                                               9.00                                        95.5 1370   2.04(2H, mc)   (69.28)                                                                            (6.46)                                                                             (8.98)                                           1410   2.40-3.15(6H, m)                                                        1480   3.72(3H, s)                                                             1600   6.66-7.40(5H, m)                                             42    63-  1300   1.23(3H, t) 8.38(1H, d)                                                                       70.13                                                                              6.75                                                                               8.67                                        64   1365   1.73(4H, mc)   (69.90)                                                                            (6.79)                                                                             (8.58)                                           1410   2.40-3.00(6H, m)                                                        1480   3.71(3H, s)                                                             1600   6.68-7.42(5H, m)                                             43    107- 1300   1.32(3H, t)    70.92                                                                              5.67                                                                               8.49                                        108  1365   2.83(2H, q)    (70.77)                                                                            (5.62)                                                                             (8.68)                                           1435   3.77(3H, s)                                                             1595   6.93-7.96(10H, m)                                            44    102- 1300   1.31(3H, t)    69.40                                                                              6.52                                                                               9.02                                        103.5                                                                               1370   2.05(2H, mc)   (69.28)                                                                            (6.46)                                                                             (8.98)                                           1435   2.60-3.10(6H, m)                                                        1590   3.73(3H, s)                                                                    6.68-7.80(6H, m)                                             45    102- 1300   1.30(3H, t)    69.77                                                                              6.77                                                                               8.61                                        103  1375   1.73(4H, mc)   (69.90)                                                                            (6.79)                                                                             (8.58)                                           1445   2.50-3.10(6H, m)                                                        1595   3.72(3H, s)                                                                    6.68-7.77(6H, m)                                             46    113- 1300   1.28(9H, s)    69.90                                                                              7.33                                                                               8.45                                        114  1375   1.30(3H, t)    (69.48)                                                                            (7.37)                                                                             (8.53)                                           1445   2.82(2H, q)                                                             1475   3.73(3H, s)                                                             1590   6.82-7.76(7H, m)                                             47    108- 1300   2.13(3H, s)    70.92                                                                              5.65                                                                               9.05                                        109  1355   2.41(3H, s)    (70.77)                                                                            (5.62)                                                                             (8.68)                                           1420   3.71(3H, s)                                                             1460   7.01-7.90(9H, m)                                                        1580                                                                48    102.5-                                                                              1300   2.02(2H, mc) 6.66-7.56(5H, m)                                                                 69.59                                                                              6.52                                                                               9.01                                        104  1360   2.23(3H, s)    (69.28)                                                                            (6.46)                                                                             (8.98)                                           1430   2.46(3H, s)                                                             1465   2.86(4H, t)                                                             1580   3.68(3H, s)                                                  49    98-  1300   1.73(4H, mc) 6.65-7.56(5H, m)                                                                 70.21                                                                              6.76                                                                               8.61                                        99.5 1360   2.25(3H, s)    (69.90)                                                                            (6.79)                                                                             (8.58)                                           1430   2.46(3H, s)                                                             1460   2.71(4H, mc)                                                            1580   3.68(3H, s)                                                  50    150- 1305   1.28(9H, s)    69.57                                                                              7.32                                                                               8.50                                        151.5                                                                               1380   2.24(3H, s)    (69.48)                                                                            (7.37)                                                                             (8.53)                                           1460   2.46(3H, s)                                                             1580   3.70(3H, s)                                                                    6.80-7.53(6H, m)                                             51    85.5-                                                                               1320 1595                                                                             1.20(9H, s)    65.15                                                                              6.69                                                                               8.44                                        86.5 1365   3.70(3H, s)    (65.43)                                                                            (6.71)                                                                             (8.48)                                           1420   3.86(3H, s)                                                             1460   6.43-7.71(7H, m)                                                        1570                                                                52    81-  1310 1590                                                                             1.31(9H, s)    69.05                                                                              7.11                                                                               8.94                                        82   1350 1720                                                                             3.58(3H, s)    (68.77)                                                                            (7.05)                                                                             (8.91)                                           1410   3.90(3H, s)                                                             1460   6.33-7.70(7H, m)                                                        1575                                                                53    143- 1300   1.28(9H, s)    54.20                                                                              5.13                                                                               7.48                                        144  1365   3.73(3H, s)    (53.83)                                                                            (5.05)                                                                             (7.39)                                           1425   6.76-7.63(7H, m)                                                        1470                                                                           1570                                                                54    126.5-                                                                              1300   1.23(9H,s)     60.72                                                                              5.77                                                                               8.47                                        128  1365   3.68(3H, s)    (60.98)                                                                            (5.72)                                                                             (8.37)                                           1415   6.73-7.63(7H, m)                                                        1460                                                                           1575                                                                55    86-  1310 1720                                                                             0.66(3H, t) 6.33-7.73(7H, m)                                                                  69.33                                                                              7.34                                                                               8.45                                        87   1345   1.25(6H, s)    (69.49)                                                                            (7.37)                                                                             (8.53)                                           1415   1.60(2H, q)                                                             1460   3.56(3H, s)                                                             1585   3.90(3H, s)                                                  56    52-  1320   0.81(3H, t) 6.33-7.73(7H, m)                                                                  65.17                                                                              6.63                                                                               8.55                                        53   1365   1.20(3H, d) 6.50-7.70(7H, m)                                                                  (65.43)                                                                            (6.71)                                                                             (8.48)                                           1415   1.56(2H, p)                                                             1460   2.61(1H, sex)                                                           1590   3.75(3H, s)                                                  57    74-  1365   0.75(3H, t) 3.86(3H, s)                                                                       69.08                                                                              7.07                                                                               8.94                                        75   1405   1.15(3H, d) 6.30-7.70(7H, m)                                                                  (68.77)                                                                            (7.05)                                                                             (8.91)                                           1460   1.51(2H, p)                                                             1580   2.55(1H, sex)                                                           1710   3.51(3H, s)                                                  58    55-  1320   1.17(6H, d)    64.80                                                                              6.41                                                                               8.83                                        56   1365   2.86(1H, h)    (64.54)                                                                            (6.37)                                                                             (8.86)                                           1410   3.69(3H, s)                                                             1460   3.86(3H, s)                                                             1595   6.47-7.85(7H, m)                                             59    64-  1350   1.25(6H, d)    68.25                                                                              6.63                                                                               9.16                                        65   1410   2.91(1H, h)    (67.98)                                                                            (6.71)                                                                             (9.33)                                           1460   3.60(3H, s)                                                             1590   3.91(3H, s)                                                             1715   6.40-7.85(7H, m)                                             60    oil  1335*  1.60(8H, mc)   70.83                                                                              6.61                                                                               8.38                                             1400   2.90(2H, s)    (70.99)                                                                            (6.55)                                                                             (8.28)                                           1455   3.59(3H, s)                                                             1575   3.92(3H, s)                                                             1725   6.40-7.60(6H, m)                                             61    oil  1320*  2.35(3H, s)    62.77                                                                              5.91                                                                               9.22                                             1360   3.74(3H, s)    (62.49)                                                                            (5.94)                                                                             (9.72)                                           1420   3.92(3H, s)                                                             1460   6.48-7.75(7H, m)                                                        1600                                                                62    oil  1320*  1.21(3H, t)    63.43                                                                              5.92                                                                               9.14                                             1360   2.65(2H, q)    (63.56)                                                                            (6.00)                                                                             (9.27)                                           1420   3.71(3H, s)                                                             1460   3.91(3H, s)                                                             1600   6.35-7.75(7H, m)                                             63    69.5-                                                                               1320   1.21(3H, t)    63.70                                                                              5.92                                                                               9.18                                        70.5 1360   2.60(2H, q)    (63.56)                                                                            (6.00)                                                                             (9.27)                                           1415   3.70(3H, s)                                                             1460   3.92(3H, s)                                                             1595   6.43-7.73(7H, m)                                             64    87-  1325   3.74(3H, s) 7.63(1H, t)                                                                       47.76                                                                              3.69                                                                               7.83                                        88   1370   3.93(3H, s)    (47.60)                                                                            (3.70)                                                                             (7.93)                                           1420   6.67(1H, d)                                                             1455   6.85-7.15(3H, m)                                                        1595   7.49(2H, d)                                                  65    87-  1350   3.50(3H, s)    49.77                                                                              3.81                                                                               8.04                                        88   1405   3.86(3H, s)    (49.87)                                                                            (3.88)                                                                             (8.30)                                           1455   6.48(1H, d)                                                             1570   6.86-7.70(6H, m)                                                        1705                                                                66    73.5-                                                                               1320   2.38(6H, s) 6.95(1H, d)                                                                       50.49                                                                              4.46                                                                               7.06                                        75   1360   3.74(3H, s) 7.57(1H, t)                                                                       (50.40)                                                                            (4.47)                                                                             (7.34)                                           1410   3.93(3H, s)                                                             1445   6.62(1H, d)                                                             1580   6.80(2H, s)                                                  67    64.5-                                                                               1320   2.33(6H, s) 7.01(1H, d)                                                                       57.03                                                                              5.17                                                                               8.26                                        66   1355   3.75(3H, s) 7.63(1H, t)                                                                       (57.05)                                                                            (5.08)                                                                             (8.31)                                           1415   3.93(3H, s)                                                             1455   6.68(1H, d)                                                             1590   6.85(2H, s)                                                  68    oil  1330*  1.48(6H, mc)   58.04                                                                              4.60                                                                               7.45                                             1410   3.35(2H, s)    (57.92)                                                                            (4.66)                                                                             (7.50)                                           1440   3.57(3H, s)                                                             1570   6.65-6.90(6H, m)                                                        1710                                                                69    135- 1300 1500                                                                             3.00(6H, s)    67.32                                                                              5.58                                                                               12.31                                       136  1360   3.73(3H, s)    (67.62)                                                                            (5.67)                                                                             (12.45)                                          1415   6.28(1H, d)                                                             1460   6.65(1H, d)                                                             1555   7.10-7.97(8H, m)                                             70    108- 1300 1595                                                                             1.72(4H, mc) 6.50-7.19(4H, m)                                                                 67.13                                                                              6.69                                                                               12.62                                       109.5                                                                               1360   2.69(4H, mc) 7.42(1H, t)                                                                      (66.83)                                                                            (6.78)                                                                             (12.30)                                          1420   3.02(6H, s)                                                             1460   3.71(3H, s)                                                             1555   6.30(1H, d)                                                  71    83-  1300 1595                                                                             1.97(2H, p) 6.48-7.27(4H, m)                                                                  66.34                                                                              6.52                                                                               13.15                                       84   1360   2.80(4H, t) 7.41(1H, t)                                                                       (66.02)                                                                            (6.46)                                                                             (12.83)                                          1415   2.98(6H, s)                                                             1465   3.66(3H, s)                                                             1555   6.29(1H, d)                                                  72    89.5-                                                                               1375   1.31(9H, s) 7.00(2H, d)                                                                       66.56                                                                              7.26                                                                               12.23                                       90.5 1420   3.06(6H, s) 7.20-7.63(3H, m)                                                                  (66.43)                                                                            (7.33)                                                                             (12.23)                                          1475   3.75(3H, s)                                                             1555   6.37(1H, d)                                                             1595   6.63(1H, d)                                                  73    88-  1310   1.26(9H, s)    67.75                                                                              6.65                                                                               9.43                                        89.5 1370   3.73(3H, s)    (67.97)                                                                            (6.71)                                                                             (9.32)                                           1420   6.71-7.90(7H, m)                                                        1470   8.37-8.62(1H, m)                                                        1585                                                                74    65-  1290   1.26(s) 1.31(s) (9H)                                                                          68.58                                                                              7.10                                                                               8.99                                        67.5 1375   2.36(3H, s) 8.26-8.51(1H, m)                                                                  (68.75)                                                                            (7.05)                                                                             (8.91)                                           1415   3.56(0.6H, s)                                                           1480   3.65(2.4H, s)                                                           1575   6.65-7.75(6H, m)                                             75    96-  1295   1.28(9H, s)    69.02                                                                              6.96                                                                               8.84                                        98   1370   2.35(3H, s)    (68.75)                                                                            (7.05)                                                                             (8.91)                                           1400   3.70(3H, s)                                                             1480   6.72-7.45(6H, m)                                                        1605   8.34(1H, d)                                                  76    94-  1310   1.27(9H, s)    68.43                                                                              7.03                                                                               8.97                                        95.5 1385   2.30(3H, s)    (68.75)                                                                            (7.05)                                                                             (8.91)                                           1480   3.71(3H, s)                                                             1580   6.70-7.67(6H, m)                                                               8.32(1H, bs)                                                 77    116- 1305   1.27(9H, s)    68.46                                                                              6.99                                                                               9.00                                        117.5                                                                               1370   2.53(3H, s)    (68.75)                                                                            (7.05)                                                                             (8.91)                                           1440   3.71(3H, s)                                                             1480   6.70-7.75(7H, m)                                                        1595                                                                78    76-  1325   1.28(9H, s)    69.84                                                                              7.37                                                                               8.59                                        77   1385   2.30(3H, 2)    (69.48)                                                                            (7.36)                                                                             (8.53)                                           1480   2.49(3H, s)                                                             1610   3.69(3H, s)                                                                    6.72-7.45(6H, m)                                             79    98-  1300   1.28(9H, s)    69.73                                                                              7.44                                                                               8.60                                        99   1360   2.27(3H, s)    (69.48)                                                                            (7.36)                                                                             (8.53)                                           1450   2.48(3H, s)                                                             1580   3.70(3H, s)                                                                    6.70-7.56(6H, m)                                             80    104.4-                                                                              1300   1.28(9H, s)    69.26                                                                              7.32                                                                               8.61                                        106  1380   1.31(3H, t)    (69.48)                                                                            (7.36)                                                                             (8.53)                                           1440   2.82(2H, q)                                                             1480   3.73(3H, s)                                                             1595   6.70-7.80(7H, m)                                             81    68-  1340 1715                                                                             1.28(9H, s)    69.37                                                                              7.54                                                                               12.95                                       69   1405   3.02(6H, s)    (69.69)                                                                            (7.69)                                                                             (12.83)                                          1500   3.53(3H, s)                                                             1560   6.22(1H, d)                                                             1590   6.85-7.60(6H, m)                                             82    64-  1320   2.30(6H, s)    63.51                                                                              6.15                                                                               9.55                                        65   1370   3.75(3H, s)    (63.55)                                                                            (6.00)                                                                             (9.26)                                           1415   3.92(3H, s)                                                             1460   6.50-7.12(5H, m)                                                        1595   7.58(1H, t)                                                  83    93-  1325   2.35(3H, s) 7.66 (1H, t)                                                                      56.06                                                                              4.52                                            94   1370   3.76(3H, s)    (55.81)                                                                            (4.68)                                                                             (8.67)                                           1415   3.95(3H, s)                                                             1460   6.56-7.16(4H, m)                                                        1600   7.35(1H, d)                                                  84    107- 1345   2.34(3H, s)    59.02                                                                              4.95                                                                               9.06                                        108  1405   3.57(3H, s)    (58.73)                                                                            (4.92)                                                                             (9.13)                                           1455   3.92(3H, s)                                                             1575   6.51(1H, d)                                                             1710   6.75-7.73(5H, m)                                             85    107.5-                                                                              1320   0.74(6H, d) 6.62(1H, d)                                                                       66.91                                                                              7.35                                                                               7.98                                        109  1370   1.24(6H, s) 6.80-7.12(3H, m)                                                                  (67.00)                                                                            (7.31)                                                                             (7.81)                                           1420   1.93(1H, h) 7.30(2H, d)                                                 1460   3.75(3H, s) 7.58(1H, t)                                                 1595   3.93(3H, s)                                                  86    68-  1325   3.75(3H, s) 7.71(1H, t)                                                                       54.33                                                                              4.29                                                                               8.93                                        69   1370   3.95((3H, s)   (54.45)                                                                            (4.24)                                                                             (9.07)                                           1415   6.71(1H, d)                                                             1485   6.88-7.20(3H, m)                                                        1590   7.38(2H, d)                                                  87    83-  1315   1.18(3H, t) 6.50-7.27(5H, m)                                                                  64.52                                                                              6.45                                                                               8.68                                        85   1360   2.27(3H, s) 7.56(1H, t)                                                                       (64.53)                                                                            (6.37)                                                                             (8.85)                                           1405   2.59(2H, q)                                                             1450   3.75(3H, s)                                                             1590   3.92(3H, s)                                                  88    61-  1350   1.18(3H, t) 6.48(1H, d)                                                                       67.92                                                                              6.63                                                                               9.20                                        62   1415   2.28(3H, s) 6.75-7.77(5H, m)                                                                  (67.98)                                                                            (6.71)                                                                             (9.32)                                           1465   2.59(2H, q)                                                             1585   3.57(3H, s)                                                             1720   3.91(3H, s)                                                  89    93-  1315 1590                                                                             2.54(6H, s)    61.91                                                                              5.56                                                                               8.53                                        94   1360 1680                                                                             3.73(3H, s)    (61.79)                                                                            (5.49)                                                                             (8.47)                                           1405   3.91(3H, s)                                                             1445   6.63(1H, d)                                                             1560   6.85-7.86(5H, m)                                             90    oil  1330*  1.20(6H, d) 6.58(1H, d)                                                                       65.47                                                                              6.68                                                                               8.18                                             1370   2.16(3H, s) 6.75-7.25(4H, m)                                                                  (65.42)                                                                            (6.71)                                                                             (8.47)                                           1425   2.84(1H, h) 7.55(1H, t)                                                 1470   3.70(3H, s)                                                             1605   3.87(3H, s)                                                  91    80-  1320   0.88(6H, d)    65.69                                                                              6.82                                                                               8.23                                        81.5 1365   1.45-2.23(1H, m)                                                                              (65.42)                                                                            (6.71)                                                                             (8.47)                                           1420   2.46(2H, d) 6.62(1H, d)                                                 1460   3.75(3H, s) 6.78-7.26(5H, m)                                            1595   3.92(3H, s) 7.58(1H, t)                                      92    67-  1315   1.21(6H, d) 6.65(1H, d)                                                                       65.25                                                                              6.57                                                                               8.29                                        68   1350   2.32(3H, s) 6.80-7.40(4H, m)                                                                  (65.42)                                                                            (6.71)                                                                             (8.47)                                           1400   3.12(1H, h) 7.55(1H, t)                                                 1440   3.76(3H, s)                                                             1590   3.94(3H, s)                                                  93    88-  1340   1.21(6H, d) 6.48(1H, d)                                                                       68.72                                                                              6.91                                                                               8.91                                        89   1410   2.33(3H, s) 6.76-7.73(5H, m)                                                                  (68.76)                                                                            (7.05)                                                                             (8.91)                                           1460   3.12(1H, h)                                                             1580   3.60(3H, s)                                                             1715   3.93(3H, s)                                                  94    97-  1320   1.40(9H, s) 6.73-7.12(3H, m)                                                                  66.24                                                                              6.98                                                                               8.25                                        98   1360   2.51(3H, s) 7.35(1H, d)                                                                       (66.24)                                                                            (7.02)                                                                             (8.13)                                           1420   3.75(3H, s) 7.58(1H, t)                                                 1455   3.92(3H, s)                                                             1590   6.63(1H, d)                                                  95    93-  1345   1.40(9H, s) 6.92(2H, bs)                                                                      69.36                                                                              7.36                                                                               8.73                                        94.5 1405   2.53(3H, s) 7.16-7.68(3H, m)                                                                  (69.48)                                                                            (7.36)                                                                             (8.53)                                           1455   3.59(3H, s)                                                             1580   3.92(3H, s)                                                             1710   6.48(1H, d)                                                  96    81-  1325   3.75(3H, s) 7.60(1H, t)                                                                       52.48                                                                              3.99                                                                               8.09                                        82   1375   3.93(3H, s) 7.62(2H, d)                                                                       (52.62)                                                                            (3.82)                                                                             (8.18)                                           1410   6.65(1H, d)                                                             1460   6.95(1H, d)                                                             1600   7.17(2H, d)                                                  97    85-  1320   3.58(3H, s)    55.21                                                                              4.21                                                                               8.87                                        86   1415   3.92(3H, s)    (55.21)                                                                            (4.01)                                                                             (8.58)                                           1470   6.52(1H, d)                                                             1580   7.15-7.80(6H, m)                                                        1715                                                                98    91-  1340 1480                                                                             3.76(3H, s) 7.67(1H, t)                                                                       52.73                                                                              4.09                                                                               12.98                                       92.5 1375 1605                                                                             3.93(3H, s) 8.26(2H, d)                                                                       (52.65)                                                                            (4.10)                                                                             (13.15)                                          1405   6.71(1H, d)                                                             1425   6.98(1H, d)                                                             1460   7.25(2H, d)                                                  99    103- 1325   2.32(3H, s) 7.58(1H, t)                                                                       55.80                                                                              4.56                                                                               8.57                                        105  1365   3.73(3H, s)    (55.81)                                                                            (4.68)                                                                             (8.67)                                           1410   3.92(3H, s)                                                             1460   6.63(1H, d)                                                             1600   6.75-7.33(4H, m)                                             100   114.5-                                                                              1350   2.33(3H, s)    58.59                                                                              4.80                                                                               8.40                                        115.5                                                                               1410   3.56(3H, s)    (58.73)                                                                            (4.92)                                                                             (9.13)                                           1460   3.91(3H, s)                                                             1580   6.50(1H, d)                                                             1715   6.83-7.73(5H, m)                                             101   105.5-                                                                              1320   2.35(3H, s)    49.03                                                                              4.21                                                                               7.43                                        107  1365   3.73(3H, s)    (49.05)                                                                            (4.11)                                                                             (7.62)                                           1410   3.91(3H, s)                                                             1455   6.53-7.10(4H, m)                                                        1600   7.20-7.80(2H, m)                                             102   110- 1355   2.38(3H, s)    51.03                                                                              4.34                                                                               8.11                                        110.5                                                                               1415   3.56(3H, s)    (51.29)                                                                            (4.30)                                                                             (7.97)                                           1460   3.92(3H, s)                                                             1580   6.50(1H, d)                                                             1720   6.70-7.72(5H, m)                                             103   88.5-                                                                               1355   1.78(4H, mc) 8.85(1H, s)                                                                      57.83                                                                              4.99                                                                               12.21                                       90   1420   2.76(4H, mc)   (57.56)                                                                            (4.83)                                                                             (12.58)                                          1445   3.82(3H, s)                                                             1490   6.65-7.20(3H, m)                                                        1560   7.73(1H, s)                                                  104   oil  1350*  1.35(9H, s) 8.90(1H, s)                                                                       57.06                                                                              5.42                                                                               12.73                                            1420   3.86(3H, s)    (57.22)                                                                            (5.40)                                                                             (12.51)                                          1445   7.00(2H, d)                                                             1500   7.46(2H, d)                                                             1560   7.78(1H, s)                                                  105   110- 1335 1525                                                                             1.73(4H, mc)   53.69                                                                              4.81                                                                               10.78                                       111  1380   2.51(3H, s)    (53.74)                                                                            (4.77)                                                                             (11.06)                                          1425   2.72(4H, mc)                                                            1460   3.76(3H, s)                                                             1485   6.60-7.30(4H, m)                                             106   71-  1315   3.75(3H, s)    52.50                                                                              4.01                                                                               7.82                                        72   1370   3.92(3H, s)    (52.62)                                                                            (3.82)                                                                             (8.18)                                           1420   6.65(1H, d)                                                             1460   6.97(1H, d)                                                             1590   7.15-7.78(5H, m)                                             107   79-  1320   3.60(3H, s)    55.39                                                                              3.91                                                                               8.22                                        80   1410   3.93(3H, s)    (55.21)                                                                            (4.01)                                                                             (8.58)                                           1445   6.55(1H, d)                                                             1580   7.20-7.87(6H, m)                                                        1720                                                                108   50-  1320 1595                                                                             1.23(6H, d) 6.75-7.41(5H, m)                                                                  64.84                                                                              6.19                                                                               8.55                                        51   1360   2.92(1H, h) 7.60(1H, t)                                                                       (64.53)                                                                            (6.37)                                                                             (8.85)                                           1410   3.75(3H, s)                                                             1455   3.94(3H, s)                                                             1570   6.61(1H, d)                                                  109   58.5-                                                                               1320   3.73(3H, s)    54.38                                                                              4.16                                                                               8.73                                             1360   3.91(3H, s)    (54.45)                                                                            (4.24)                                                                             (9.07)                                           1420   6.64(1H, d)                                                             1460   6.85-7.37(5H, m)                                                        1580   7.58(1H, t)                                                  110   69-  1335   3.73(3H, s)    47.47                                                                              3.79                                                                               7.73                                        69.5 1380   3.92(3H, s)    (47.60)                                                                            (3.70)                                                                             (7.93)                                           1425   6.63(1H, d)                                                             1460   6.82-7.40(5H, m)                                                        1570   7.60(1H, t)                                                  111   103- 1360   3.57(3H, s)    49.93                                                                              3.99                                                                               8.19                                        103.5                                                                               1410   3.93(3H, s)    (49.87)                                                                            (3.88)                                                                             (8.30)                                           1460   6.53(1H, d)                                                             1580   7.03-7.70(6H, m)                                                        1715                                                                112   oil  1340*  1.56(8H, mc)   59.05                                                                              5.02                                                                               7.14                                             1415   2.99(2H, s)    (58.93)                                                                            (4.94)                                                                             (7.23)                                           1445   3.62(3H, s)                                                             1580   6.85-7.95(6H, m)                                                        1730                                                                113   78-  1320   3.73(3H, s)    49.16                                                                              3.33                                                                               7.88                                        79   1370   3.92(3H, s)    (48.99)                                                                            (3.52)                                                                             (8.16)                                           1415   6.56-7.80(6H, m)                                                        1455                                                                           1595                                                                114   134- 1300   2.34(3H, s)    58.79                                                                              4.88                                                                               9.05                                        136  1370   2.57(3H, s)    (58.72)                                                                            (4.92)                                                                             (9.13)                                           1440   3.75(3H, s)                                                             1465   6.70-7.80(6H, m)                                                        1590                                                                115   113- 1295   2.23(6H, s)    66.98                                                                              6.29                                                                               10.00                                       114  1370   2.37(3H, s)    (67.10)                                                                            (6.33)                                                                             (9.78)                                           1400   3.73(3H, s)                                                             1475   6.70-7.36(5H, m)                                                        1600   8.34(1H, d)                                                  116   oil  1320*  2.18(3H, s) 7.52(1H, t)                                                                       62.27                                                                              5.66                                                                               9.83                                             1360   3.71(3H, s)    (62.47)                                                                            (5.59)                                                                             (9.71)                                           1415   3.87(3H, s)                                                             1460   6.60(1H, d)                                                             1600   6.80-7.30(5H, m)                                             117   66.5-                                                                               1320   2.27(3H, s) 7.53(1H, t)                                                                       62.13                                                                              5.51                                                                               9.87                                        67.5 1370   3.72(3H, s)    (62.47)                                                                            (5.59)                                                                             (9.71)                                           1415   3.88(3H, s)                                                             1460   6.60(1H, d)                                                             1595   6.80-7.30(5H, m)                                             118   89-  1345   3.57(3H, s)    55.53                                                                              4.56                                                                               8.44                                        90   1410   3.85(3H, s)    (55.82)                                                                            (4.68)                                                                             (8.67)                                           1460   3.92(3H, s)                                                             1595   6.40-6.90(3H, m)                                                        1720   7.17-7.73(3H, m)                                             119   64.5-                                                                               1325   3.76(3H, s)    53.13                                                                              4.29                                                                               8.12                                        65.5 1365   3.88(3H, s)    (53.17)                                                                            (4.46)                                                                             (8.26)                                           1420   3.94(3H, s)                                                             1460   6.50-7.80(6H, m)                                                        1595                                                                120   78-  1340   3.56(3H, s)    58.52                                                                              4.94                                                                               7.80                                        79   1410   3.91(3H, s)    (58.54)                                                                            (4.91)                                                                             (8.03)                                           1460   4.56(2H, mc)                                                            1580   5.08-6.91(6H, m)                                                        1715   7.11-7.71(3H, m)                                             121   116.5-                                                                              1315   3.71(3H, s)    55.89                                                                              4.75                                                                               7.50                                        117.5                                                                               1375   3.90(3H, s)    (55.96)                                                                            (4.69)                                                                             (7.67)                                           1415   4.55(2H, mc)                                                            1460   5.01-7.43(8H, m)                                                        1590   7.60(1H, t)                                                  122   79.5-                                                                               1305 1730                                                                             2.55(1H, t) 6.66-7.81(5H, m)                                                                  58.97                                                                              4.54                                                                               8.04                                        80.5 1355   3.58(3H, s)    (58.88)                                                                            (4.36)                                                                             (8.07)                                           1410   3.91(3H, s)                                                             1460   4.75(2H, d)                                                             1575   6.55(1H, d)                                                  123   94.5-                                                                               1340 3500                                                                             2.50(1H, bt) 6.95-7.75(6H, m)                                                                 62.48                                                                              5.71                                                                               9.60                                        95.5 1405   3.57(3H, s)    (62.49)                                                                            (5.59)                                                                             (9.71)                                           1455   3.90(3H, s)                                                             1580   4.58(2H, bd)                                                            1710   6.50(1H, d)                                                  124   112- 1400   2.59(3H, s) 8.03(2H, d)                                                                       64.02                                                                              5.50                                                                               9.18                                        112.5                                                                               1460   3.61(3H, s)    (63.99)                                                                            (5.37)                                                                             (9.32)                                           1570   3.94(3H, s)                                                             1665   6.56(1H, d)                                                             1715   7.18-7.78(4H, m)                                             125   93-  1320   2.12(3H, s) 6.62(1H, d)                                                                       64.77                                                                              5.78                                                                               8.90                                        93.5 1370   3.73(3H, s) 6.77-7.75(6H, m)                                                                  (64.94)                                                                            (5.77)                                                                             (8.91)                                           1415   3.92(3H, s)                                                             1455   5.05(1H, bs)                                                            1595   5.33(1H, bs)                                                 126   110.5-                                                                              1345 1600                                                                             3.75(3H, s) 7.50-7.82(3H, m)                                                                  60.25                                                                              4.43                                                                               14.10                                       111.5                                                                               1385 2250                                                                             3.93(3H, s)    (60.18)                                                                            (4.37)                                                                             (14.03)                                          1415   6.68(1H, d)                                                             1440   6.97(1H, d)                                                             1470   7.18(2H, d)                                                  127   oil  1330 1560                                                                             1.26(9H, s) 8.46(1H, d)                                                                       56.89                                                                              5.56                                                                               12.78                                            1360*  3.80(3H, s)    (57.22)                                                                            (5.40)                                                                             (12.51)                                          1410   6.93(2H, d)                                                             1460   7.39(2H, d)                                                             1500   7.63(1H, d)                                                  128   104- 1320 3400                                                                             1.33(9H, s) 8.43(1H, d)                                                                       58.00                                                                              5.85                                                                               14.87                                       105  1410   3.18(3H, d)    (57.73)                                                                            (5.92)                                                                             (14.96)                                          1455   3.86(3H, s)                                                             1575   6.80-7.50(5H, m)                                                        1600   8.36(1H, bs)                                                 129   133- 1335 1600                                                                             1.25(9H, s) 8.34(1H, d)                                                                       57.41                                                                              5.77                                                                               14.62                                       133.5                                                                               1380 3400                                                                             3.09(3H, d)    (57.73)                                                                            (5.92)                                                                             (14.96)                                          1435   3.77(3H, s)                                                             1495   6.73-7.50(5H, m)                                                        1575   8.26(1H, bs)                                                 130   122.5-                                                                              1340 1605                                                                             1.70(4H, mc) 8.23(1H, bs)                                                                     58.28                                                                              5.31                                                                               14.72                                       123  1380   2.68(4H, mc) 8.32(1H, d)                                                                      (58.04)                                                                            (5.41)                                                                             (15.04)                                          1430   3.08(3H, d)                                                             1490   3.76(3H, s)                                                             1575   6.59-7.37(4H, m)                                             131   oil  1355*  1.23(9H, s) 6.70-7.57(5H, m)                                                                  66.46                                                                              7.28                                                                               12.17                                            1410   2.98(6H, s)    (66.43)                                                                            (7.33)                                                                             (12.23)                                          1465   3.68(3H, s)                                                             1550   6.28(1H, d)                                                             1590   6.58(1H, d)                                                  132   113- 1340 3400                                                                             1.20(9H, s) 6.58(1H, d)                                                                       65.57                                                                              6.88                                                                               12.84                                       114  1375   2.80(3H, d) 6.92(2H, d)                                                                       (65.62)                                                                            (7.03)                                                                             (12.75)                                          1410   3.61(3H, s) 7.10-7.60(3H, m)                                            1470   4.57(1H, bq)                                                            1605   6.18(1H, d)                                                  133   73-  1375 3270                                                                             1.22(9H, s) 6.50-7.60(6H, m)                                                                  65.33                                                                              6.96                                                                               12.44                                       74   1420   2.82(3H, d)    (65.62)                                                                            (7.03)                                                                             (12.75)                                          1460   3.63(3H, s)                                                             1575   4.69(1H, bq)                                                            1605   6.20(1H, d)                                                  134   78-  1305 1720                                                                             3.50(3H, s) 7.02-7.67(3H, m)                                                                  62.58                                                                              5.48                                                                               9.91                                        79   1340   3.68(3H, s)    (62.49)                                                                            (5.59)                                                                             (9.71)                                           1410   3.83(3H, s)                                                             1460   6.43(1H, d)                                                             1580   6.55-6.83(3H, m)                                             135   64.5-                                                                               1320   3.73(6H s)     59.18                                                                              5.39                                                                               8.99                                        65   1365   3.90(3H, s)    (59.19)                                                                            (5.29)                                                                             (9.20)                                           1415   6.50-7.40(6H, m)                                                        1460   7.55(1H, t)                                                             1580                                                                136   91.5-                                                                               1305 1570                                                                             3.55(3H, s)    62.37                                                                              5.57                                                                               9.70                                        92   1345 1715                                                                             3.73(3H s)     (62.49)                                                                            (5.59)                                                                             (9.71)                                           1405   3.88(3H, s)                                                             1455   6.46(1H, d)                                                             1495   6.65-7.70(6H, m)                                             137   97.5-                                                                               1325 1600                                                                             3.70(6H, s)    59.26                                                                              5.47                                                                               9.48                                        98.5 1370   3.87(3H, s)    (59.19                                                                             (5.29)                                                                             (9.20)                                           1420   6.58(1H, d)                                                             1460   6.75-7.12(5H, m)                                                        1500   7.53(1H, t)                                                  138   68-  1310 1720                                                                             1.36(3H, t) 7.05-7.70(3H, m)                                                                  63.24                                                                              6.11                                                                               9.06                                        69   1345   3.56(3H, s)    (63.56)                                                                            (6.00)                                                                             (9.26)                                           1410   3.88(3H, s)                                                             1465   3.98(2H, q)                                                             1585   6.37-6.90(4H, m)                                             139   66-  1320   1.32(3H, t) 7.55(1H, t)                                                                       60.40                                                                              5.70                                                                               8.61                                        66.5 1380   3.70(3H, s)    (60.35)                                                                            (5.69)                                                                             (8.79)                                           1420   3.88(3H, s)                                                             1465   3.95(2H, q)                                                             1600   6.50-7.38(6H, m)                                             140   84-  1345 1715                                                                             1.33(3H, t) 6.70-7.67(6H, m)                                                                  63.69                                                                              5.95                                                                               9.53                                        85   1405   3.54(3H, s)    (63.56)                                                                            (6.00)                                                                             (9.26)                                           1460   3.87(3H, s)                                                             1500   3.93(2H, q)                                                             1575   6.43(1H, d)                                                  141   96.5-                                                                               1320 1600                                                                             1.35(3H, t) 7.55(1H, t)                                                                       60.08                                                                              5.53                                                                               8.87                                        97.5 1365   3.72(3H, s)    (60.35)                                                                            (5.69)                                                                             (8.79)                                           1415   3.89(3H, s)                                                             1465   3.96(2H, q)                                                             1505   6.50-7.12(6H, m)                                             142   53-  1305 1735                                                                             0.75-2.00(7H, m)                                                                              65.39                                                                              6.72                                                                               8.36                                        54   1345   3.57(3H, s) 6.60-6.90(3H, m)                                                                  (65.43)                                                                            (6.71)                                                                             (8.47)                                           1415   3.90(3H, s) 7.06-7.70(3H, m)                                            1465   3.93(2H, t)                                                             1585   6.48(1H, d)                                                  143   oil  1320*  0.70-2.00(7H, m)                                                                              62.64                                                                              6.56                                                                               7.76                                             1360   3.73(3H, s)    (62.40)                                                                            (6.40)                                                                             (8.08)                                           1420   3.90(2H, t)                                                             1460   3.91(3H, s)                                                             1600   6.45-7.70(7H, m)                                             144   62-  1340 1720                                                                             0.73-2.00(7H, m)                                                                              65.38                                                                              6.81                                                                               8.46                                        62.5 1405   3.53(3H, s) 6.70-7.67(6H, m)                                                                  (65.43)                                                                            (6.71)                                                                             (8.47)                                           1455   3.87(3H, s)                                                             1500   3.89(2H, t)                                                             1575   6.45(1H, d)                                                  145   68-  1320 1600                                                                             0.75-2.00(7H, m)                                                                              62.57                                                                              6.30                                                                               8.14                                        69   1360   3.72(3H, s) 6.77-7.12(5H, m)                                                                  (62.40)                                                                            (6.40)                                                                             (8.08)                                           1415   3.88(2H, t) 7.57(1H, t)                                                 1465   3.90(3H, s)                                                             1505   6.60(1H, d)                                                  146   oil  1320 3380                                                                             1.38(3H, d) 6.59(1H, d)                                                                       60.27                                                                              5.56                                                                               9.04                                             1360*  3.03(1H, bs) 6.80-7.15(3H, m)                                                                 (60.35)                                                                            (5.69)                                                                             (8.79)                                           1415   3.71(3H, s) 7.30(2H, d)                                                 1460   3.88(3H, s) 7.57(1H, t)                                                 1595   4.76(1H, q)                                                  147   69.5-                                                                               1320   1.28(9H, s) 6.73-7.33(5H, m)                                                                  66.01                                                                              6.93                                                                               8.32                                        71   1360   1.35(3H, t) 7.54(1H, t)                                                                       (66.24)                                                                            (7.02)                                                                             (8.13)                                           1435   3.72(3H, s)                                                             1570   4.33(2H, q)                                                             1590   6.57(1H, d)                                                  148   106.5-                                                                              1320   2.43(3H, s) 7.25(2H, d)                                                                       55.98                                                                              4.85                                                                               8.66                                        108  1360   3.73(3H, s) 7.58(1H, t)                                                                       (56.22)                                                                            (5.03)                                                                             (8.74)                                           1410   3.91(3H, s)                                                             1460   6.62(1H, d)                                                             1595   6.85-7.10(3H, m)                                             149   102.5-                                                                              1330   3.73(3H, s)    56.84                                                                              4.54                                                                               8.97                                        103.5                                                                               1375   3.93(3H, s)    (56.59)                                                                            (4.43)                                                                             (8.79)                                           1420   5.96(2H, s)                                                             1480   6.40-7.10(5H, m)                                                        1600   7.61(1H, t)                                                  150   120- 1305   2.32(3H, s)    57.52                                                                              4.37                                                                               9.79                                        122.5                                                                               1375   2.73(3H, s)    (57.43)                                                                            (4.47)                                                                             (9.56)                                           1425   6.70-7.90(6H, m)                                                        1470   8.50(1H, d)                                                             1590                                                                151   82-  1305   2.33(6H, s)    58.47                                                                              4.81                                                                               8.93                                        83.5 1380   3.70(3H, s)    (58.72)                                                                            (4.92)                                                                             (9.13)                                           1470   6.68-7.70(5H, m)                                                        1580   8.30(1H, bs)                                                 152   96-  1285   2.28(3H, s) 8.34(1H, d)                                                                       58.77                                                                              4.96                                                                               9.25                                        98   1375   2.34(3H, s)    (58.72)                                                                            (4.92)                                                                             (9.13)                                           1415   3.55(0.75H, s)                                                          1470   3.63(2.25H, s)                                                          1575   6.60-7.73(5H, m)                                             153   97-  1300   1.30(3H, t) 7.62(1H, t)                                                                       59.91                                                                              5.24                                                                               8.61                                        98.5 1370   2.33(3H, s)    (59.89)                                                                            (5.34)                                                                             (8.73)                                           1435   2.82(2H, q)                                                             1470   3.73(3H, s)                                                             1590   6.70-7.43(5H, m)                                             154   116- 1315   2.26(3H, s)    59.74                                                                              5.19                                                                               8.79                                        118  1375   2.32(3H, s)    (59.89)                                                                            (5.34)                                                                             (8.73)                                           1440   2.48(3H, s)                                                             1575   3.70(3H, s)                                                                    6.66-7.60(5H, m)                                             155   88-  1325   2.23(6H, s)    60.03                                                                              5.43                                                                               8.61                                        89.5 1380   2.50(3H, s)    (59.89)                                                                            (5.34)                                                                             (8.73)                                           1445   3.68(3H, s)                                                             1475   6.69-7.40(5H m)                                                         1605                                                                156   114- 1300   2.28(3H, s)    51.42                                                                              3.61                                                                               8.70                                        115.5                                                                               1370   3.69(3H, s)    (51.38)                                                                            (3.69)                                                                             (8.56)                                           1420   6.65-7.50(5H, m)                                                        1470   7.65(1H, t)                                                             1580                                                                157   81-  1295   2.32(3H, s) 6.70-7.00(2H, m)                                                                  57.38                                                                              5.41                                                                               12.27                                       83   1360   3.06(6H, s) 7.15-7.63(2H, m)                                                                  (57.22)                                                                            (5.40)                                                                             (12.51)                                          1415   3.71(3H, s)                                                             1460   6.36(1H, d)                                                             1595   6.58(1H, d)                                                  158   73-  1310   1.35(3H, t) 7.58(1H, t)                                                                       57.10                                                                              5.24                                                                               8.37                                        74.5 1365   2.31(3H, s)    (57.05)                                                                            (5.08)                                                                             (8.31)                                           1395   3.91(3H, s)                                                             1460   4.31(2H, q)                                                             1580   6.53-7.43(5H, m)                                             159   oil  1385 1575                                                                             1.28(9H, s)    62.18                                                                              6.17                                                                               8.03                                             1425*  1.32(3H, t)    (61.96)                                                                            (6.06)                                                                             (8.02)                                           1460   4.32(2H, q)                                                             1500   6.82-7.78(7H, m)                                                        1560                                                                160   oil  1390*  1.29(9H, s)    61.99                                                                              5.94                                                                               7.80                                             1420   1.33(3H, t)    (61.96)                                                                            (6.06)                                                                             (8.02)                                           1460   4.34(2H, q)                                                             1555   6.74-7.81(7H, m)                                                        1575                                                                161   57-  1310 1560                                                                             1.30(9H, s) 6.82-7.14(3H, m)                                                                  65.85                                                                              6.92                                                                               8.46                                        58   1350 1595                                                                             1.35(3H, t) 7.35(2H, d)                                                                       (66.24)                                                                            (7.02)                                                                             (8.13)                                           1405   3.91(3H, s) 7.54(1H, t)                                                 1460   4.32(2H, q)                                                             1495   6.61(1H, d)                                                  162   75.5-                                                                               1320 1595                                                                             1.30(9H, s) 6.73-7.35(5H, m)                                                                  65.95                                                                              7.21                                                                               8.38                                        76.5 1400   1.37(3H, t) 7.57(1H, t)                                                                       (66.24)                                                                            (7.02)                                                                             (8.13)                                           1425   3.93(3H, s)                                                             1455   4.35(2H, q)                                                             1570   6.62(1H, d)                                                  163   oil  1320 1490                                                                             1.28(3H, t) 6.43-7.15(5H, m)                                                                  66.82                                                                              6.60                                                                               7.81                                             1350 1600                                                                             1.64(4H, mc) 7.47(1H, t)                                                                      (66.63)                                                                            (6.47)                                                                             (8.18)                                           1400*  2.63(4H, mc)                                                            1425   3.82(3H, s)                                                             1465   4.23(2H, q)                                                  164   oil  1360 1575                                                                             0.95(3H, t)    63.24                                                                              6.53                                                                               7.39                                             1390*  1.32(9H, s)    (62.88)                                                                            (6.38)                                                                             (7.71)                                           1420   1.80(2H, sex)                                                           1455   4.26(2H, t)                                                             1560   6.75-7.82(7H, m)                                             165   62-  1315 1595                                                                             0.88(3H, t) 6.56(1H, d)                                                                       66.73                                                                              7.40                                                                               8.05                                        64   1420   1.23(9H, s) 6.80-7.07(3H, m)                                                                  (67.00)                                                                            (7.31)                                                                             (7.81)                                           1455   1.76(2H, sex) 7.30(2H, d)                                               1500   3.85(3H, s) 7.51(1H, t)                                                 1565   4.19(2H, t)                                                  166   oil  1320 1570                                                                             0.95(3H, t) 6.59(1H, d)                                                                       66.83                                                                              7.37                                                                               7.60                                             1360 1600                                                                             1.30(9H, s) 6.75-7.35(5H, m)                                                                  (67.00)                                                                            (7.31)                                                                             (7.81)                                           1400*  1.83(2H, sex) 7.52(1H, t)                                               1425   3.89(3H, s)                                                             1460   4.25(2H, t)                                                  167   oil  1320 1570                                                                             0.97(3H, t) 6.50-7.18(5H, m)                                                                  67.28                                                                              6.81                                                                               7.50                                             1400 1600                                                                             1.77(6H, mc) 7.53(1H, t)                                                                      (67.38)                                                                            (6.78)                                                                             (7.85)                                           1425*  2.72(4H, mc)                                                            1460   3.90(3H, s)                                                             1490   4.25(2H, t)                                                  168   oil  1305 1560                                                                             1.32(6H, d) 6.82-7.83(6H, m)                                                                  66.90                                                                              7.34                                                                               7.63                                             1345 1595                                                                             1.33(9H, s)    (67.00)                                                                            (7.31)                                                                             (7.81)                                           1405*  3.94(3H, s)                                                             1460   5.39(1H, h)                                                             1500   6.71(1H, d)                                                  169   oil  1315*  1.26(6H d)     66.91                                                                              7.49                                                                               8.09                                             1350   1.28(9H, s)    (67.00)                                                                            (7.31)                                                                             (7.81)                                           1410   3.91(3H, s)                                                             1465   5.37(1H, h)                                                             1600   6.53-7.79(7H, m)                                             170   oil  1310 1600                                                                             1.25(6H, d) 6.53-7.21(5H, m)                                                                  67.48                                                                              6.73                                                                               7.89                                             1350*  1.70(4H, mc) 7.55(1H, t)                                                                      (67.38)                                                                            (6.78)                                                                             (7.85)                                           1405   2.68(4H, mc)                                                            1465   3.87(3H, s)                                                             1490   5.32(1H, h)                                                  171   53-  1305 1710                                                                             0.75(3H, t) 6.32(1H, d)                                                                       67.81                                                                              6.68                                                                               9.19                                        55   1340   1.46(2H, sex) 6.75-7.55(6H, m)                                                                (67.98)                                                                            (6.71)                                                                             (9.32)                                           1410   2.41(2H, t)                                                             1460   3.40(3H, s)                                                             1580   3.73(3H, s)                                                  172   40-  1320 1600                                                                             0.90(3H, t) 6.58(1H, d)                                                                       64.49                                                                              6.31                                                                               8.97                                        42   1360   1.60(2H, sex) 6.78-7.33(5H, m)                                                                (64.53)                                                                            (6.37)                                                                             (8.85)                                           1420   2.56(2H, t) 7.53(1H, t)                                                 1460   3.72(3H, s)                                                             1570   3.89(3H, s)                                                  173   85.5-                                                                               1300 1575                                                                             2.60(3H, s) 7.58(1H, t)                                                                       56.70                                                                              4.75                                                                               13.32                                       87   1340 1720                                                                             3.58(3H, s) 8.01(1H, d)                                                                       (56.78)                                                                            (4.76)                                                                             (13.24)                                          1405   3.92(3H, s)                                                             1455   6.53(1H, d)                                                             1505   6.93- 7.37(3H, m)                                            174   59-  1320 1515                                                                             2.59(3H, s) 7.63(1H, t)                                                                       53.90                                                                              4.45                                                                               12.78                                       61   1340 1580                                                                             3.74(3H, s) 8.06(1H, d)                                                                       (54.04)                                                                            (4.53)                                                                             (12.60)                                          1370   3.92(3H, s)                                                             1420   6.68(1H, d)                                                             1460   6.88-7.30(3H, m)                                             175   78-  1325   2.31(3H, s) 6.77-7.25(4H, m)                                                                  57.59                                                                              5.53                                                                               8.60                                        79   1360   2.42(3H, s) 7.56(1H, t)                                                                       (57.45)                                                                            (5.42)                                                                             (8.37)                                           1420   3.73(3H, s)                                                             1465   3.91(3H, s)                                                             1620   6.58(1H, d)                                                  176   76-  1320   3.77(3H, s)    53.63                                                                              3.67                                                                               9.04                                        77.5 1375   6.93-8.00(7H, m)                                                                              (53.84)                                                                            (3.55)                                                                             (8.96)                                           1425   8.53(1H, d)                                                             1465                                                                           1585                                                                177   121- 1330 1595                                                                             2.56(3H, s)    55.42                                                                              4.11                                                                               8.38                                        122.5                                                                               1380   3.73(3H, s)    (55.20)                                                                            (4.01)                                                                             (8.58)                                           1445   6.93-7.83(7H, m)                                                        1470                                                                           1480                                                                178   95.5-                                                                               1320   2.53(3H, s)    55.06                                                                              4.19                                                                               8.97                                        97   1390   3.73(3H, s)    (55.20)                                                                            (4.01)                                                                             (8.58)                                           1480   7.00-7.83(6H, m)                                                        1595   8.40(1H, bs)                                                 179   94-  1330   2.38(3H, s)    54.92                                                                              4.11                                                                               8.41                                        96   1385   3.72(3H, s)    (55.20)                                                                            (4.01)                                                                             (8.58)                                           1415   6.95-7.77(6H, m)                                                        1480   8.37(1H, d)                                                             1605                                                                180   oil  1325*  2.37(3H, s)    55.15                                                                              3.90                                                                               8.26                                             1385   3.60(0.5H, s)  (55.20)                                                                            (4.01)                                                                             (8.58)                                           1420   3.66(2.5H, s)                                                           1485   6.96-7.83(6H, m)                                                        1610   8.40(1H, d)                                                  181   100.5-                                                                              1330   2.27(3H, s)    56.16                                                                              4.48                                                                               8.44                                        103  1380   2.49(3H, s)    (56.46)                                                                            (4.44)                                                                             (8.23)                                           1480   3.72(3H, s)                                                             1580   7.00-7.80(6H, m)                                             182   100- 1320   2.33(3H, s) 7.15(2H, d)                                                                       56.57                                                                              4.44                                                                               8.15                                        102.5                                                                               1385   2.50(3H, s) 7.58(2H, d)                                                                       (56.46)                                                                            (4.44)                                                                             (8.23)                                           1410   3.72(3H, s)                                                             1485   6.90(1H, s)                                                             1605   7.00(1H, s)                                                  183   78.5-                                                                               1320   1.30(3H, t)    56.59                                                                              4.63                                                                               8.11                                        80   1375   2.83(2H, q)    (56.46)                                                                            (4.44)                                                                             (8.23)                                           1440   3.75(3H, s)                                                             1480   6.93-7.87(7H, m)                                                        1595                                                                184   128.5-                                                                              1325   3.78(3H, s)    48.39                                                                              3.07                                                                               7.88                                        130  1375   7.03-7.95(7H, m)                                                                              (48.49)                                                                            (2.90)                                                                             (8.07)                                           1430                                                                           1480                                                                           1580                                                                185   133- 1330   3.77(3H, s)    42.96                                                                              2.52                                                                               7.34                                        135  1380   7.03-7.83(7H, m)                                                                              (42.98)                                                                            (2.57)                                                                             (7.16)                                           1435                                                                           1485                                                                           1580                                                                186   74-  1335   3.07(6H, s)    53.80                                                                              4.46                                                                               11.66                                       76   1375   3.72(3H, s)    (54.07)                                                                            (4.53)                                                                             (11.82)                                          1430   6.38(1H, d)                                                             1485   6.58(1H, d)                                                             1605   7.00-7.78(7H, m)                                             187   132- 1305   2.32(3H, s)    45.19                                                                              3.31                                                                               7.33                                        134  1375   3.71(3H, s)    (45.24)                                                                            (3.25)                                                                             (7.53)                                           1420   6.67-7.70(6H, m)                                                        1470                                                                           1580                                                                188   111- 1325   2.90(6H, s)    60.78                                                                              6.05                                                                               13.37                                       113  1360   3.73(3H, s)    (60.54)                                                                            (6.03)                                                                             (13.23)                                          1425   3.90(3H, s)                                                             1450   6.30-7.36(6H, m)                                                        1600   7.58(1H, t)                                                  189   75-  1350 1720                                                                             2.90(6H, s)    63.71                                                                              6.24                                                                               13.71                                       76   1415   3.57(3H, s)    (63.77)                                                                            (6.35)                                                                             (13.94)                                          1465   3.89(3H, s)                                                             1505   6.37-6.67(4H, m)                                                        1590   7.00-7.70(3H, m)                                             190   52-  1350   3.57(3H, s)    62.86                                                                              4.83                                                                               9.80                                        54   1415   3.90(3H, s)    (62.93)                                                                            (4.92)                                                                             (9.78)                                           1465   6.51(1H, d)                                                             1585   6.97-8.03(6H, m)                                                        1720   9.93(1H, s)                                                  191   oil  1330*  2.00(3H, d) 6.85-7.75(6H, m)                                                                  50.35                                                                              4.36                                                                               7.50                                             1370   3.73(3H, s)    (50.40)                                                                            (4.49)                                                                             (7.34)                                           1425   3.90(3H, s)                                                             1470   5.20(1H, q)                                                             1605   6.63(1H, d)                                                  192   43-  1325   1.39(3H, t) 7.18(2H, d)                                                                       54.06                                                                              4.13                                                                               7.87                                        45   1400   3.95(3H, s) 7.62(2H, d)                                                                       (53.92)                                                                            (4.24)                                                                             (7.86)                                           1435   4.33(2H, q) 7.63(1H, t)                                                 1590   6.70(1H, d)                                                                    6.94(1H, d)                                                  193   oil  1315 1500                                                                             1.20(3H, t) 6.62(1H, d)                                                                       64.50                                                                              6.46                                                                               8.49                                             1350 1600                                                                             1.35(3H, t) 6.82-7.40(5H, m)                                                                  (64.53)                                                                            (6.37)                                                                             (8.85)                                           1400*  2.64(2H, q) 7.56(1H, t)                                                 1425   3.92(3H, s)                                                             1460   4.33(2H, q)                                                  194   53-  1310 1595                                                                             1.23(6H, d) 6.59(1H, d)                                                                       65.17                                                                              6.67                                                                               8.63                                        54   1395   1.33(3H,t) 6.77-7.35(5H, m)                                                                   (65.42)                                                                            (6.71)                                                                             (8.47)                                           1425   2.87(1H, h) 7.53(1H, t)                                                 1450   3.92(3H, s)                                                             1495   4.30(2H, q)                                                  195   oil  1325*  1.35(3H, t) 6.47-7.38(5H, m)                                                                  65.54                                                                              6.13                                                                               8.18                                             1410   2.05(2H, p) 7.55(1H, t)                                                                       (65.82)                                                                            (6.13)                                                                             (8.52)                                           1435   2.87(4H, t)                                                             1470   3.90(3H, s)                                                             1610   4.32(2H, q)                                                  196   oil  1320 1600                                                                             0.86-2.08(9H, m) 7.53(1H, t)                                                                  67.77                                                                              6.35                                                                               8.23                                             1350*  3.28(2H, bs)   (67.76)                                                                            (6.25)                                                                             (7.90)                                           1400   3.88(3H, s)                                                             1425   4.28(2H, q)                                                             1465   6.41-7.26(5H, m)                                             197   80-  1305 1585                                                                             1.37(3H, t) 8.53(1H, d)                                                                       69.56                                                                              6.27                                                                               8.70                                        82   1410   1.77(4H, mc)   (69.19)                                                                            (6.45)                                                                             (8.96)                                           1430   2.75(4H, mc)                                                            1465   4.36(2H, q)                                                             1495   6.55-7.96(6H, m)                                             198   76.5-                                                                               1305 1595                                                                             1.28(3H, t) 6.57-7.78(6H, m)                                                                  70.25                                                                              6.84                                                                               8.72                                        78.5 1350   1.72(4H, mc)   (69.90)                                                                            (6.79)                                                                             (8.58)                                           1370   2.55(3H, s)                                                             1415   2.72(4H, mc)                                                            1455   4.31(2H, q)                                                  199   70.5-                                                                               1300 1570                                                                             1.32(3H, t)    55.37                                                                              4.73                                                                               7.21                                        72.5 1350   1.75(4H, mc)   (55.24)                                                                            (4.89)                                                                             (7.15)                                           1385   2.73(4H, mc)                                                            1425   4.30(2H, q)                                                             1495   6.60-7.77(6H, m)                                             200   oil  1330 1730                                                                             1.42(3H, t) 6.53(1H, d)                                                                       69.66                                                                              6.70                                                                               8.32                                             1385*  1.82(4H, mc) 6.72-7.72(5H, m)                                                                 (69.91)                                                                            (6.79)                                                                             (8.58)                                           1440   2.80(4H, mc)                                                            1475   3.95(3H, s)                                                             1585   4.20(2H, q)                                                  201   oil  1330*  3.36(3H, s) 6.90-7.20(3H, m)                                                                  60.18                                                                              5.73                                                                               9.08                                             1375   3.75(3H, s) 7.35(2H, d)                                                                       (60.35)                                                                            (5.69)                                                                             (8.79)                                           1425   3.93(3H, s) 7.62(1H, t)                                                 1470   4.45(2H, s)                                                             1605   6.65(1H, d)                                                  202   oil  1325 1600                                                                             0.71-1.90(7H, m)                                                                              65.62                                                                              6.59                                                                               8.78                                             1365*  2.62(2H, t) 6.78-7.31(5H, m)                                                                  (65.42)                                                                            (6.71)                                                                             (8.47)                                           1420   3.75(3H, s) 7.65(1H, t)                                                 1460   3.91(3H, s)                                                             1500   6.60(1H, d)                                                  203   106- 1320 1580                                                                             3.81(3H, s)    62.53                                                                              4.79                                                                               12.63                                       108  1360   3.93(3H, s)    (62.75)                                                                            (4.64)                                                                             (12.91)                                          1415   6.67(1H, d)                                                             1455   7.08-8.33(8H, m)                                                        1565                                                                __________________________________________________________________________      *NaCl                                                                    

In order to use compounds of the present invention as herbicides, proper amount of one or more than one of the compounds represented by the above-stated general formula (I) is incorporated with inert carriers to use as usual agricultural chemicals like water dispersible powder, emulsifiable concentrate, granules, dust and so on.

As solid carriers, talc, clay, diatomaceous earth, bentonite, kaolin, Japanese acid clay, white carbon, pumice powder and the like are exemplified. As liquid carriers, water, alcohol, benzene, toluene, xylene, kerosine, cyclohexane, cyclohexanone, isophorone, Butyl Cellosolve, benzyl acetate, dimethylformamide, mineral oil and the like are used.

Furthermore, surface-active agents and stabilizers can be added when they are required. In addition, the herbicides of the present invention can be applied after incorporating them with other agricultural chemicals used in the same field, for example, insecticides, fungicides, herbicides, plant growth regulators or fertilizers. Especially, there will be occasions for the herbicides containing the compounds of the present invention that it is proper to be mixed with other herbicides for the purpose of reducing labor for spreading or for the purpose of extending the spectrum of weed species to be effectively prevented.

As herbicides to be added, triazine herbicides such as Atrazine, Simazine, Simetryn, Prometryn and the like; carbamate herbicides such as Asulam, Benthiocarb, Molinate and the like; urea herbicides such as Linuron, Dymrone and the like; phenoxy-series herbicides such as 2,4-D, MCP, MCPB, Naproanilide and the like; diphenyl ether herbicides such as Nitrofen, Chlornitrofen, Chlomethoxynil and the like; heterocyclic-series herbicides such as Oxadiazon, Pyrazolate, Bentazon and the like; and amide herbicides such as Alachlor, Butachlor, Propanil and the like can be exemplified. It is possible to provide mixtures of the compounds of the present invention by being skillfully combined with one or more than one of the herbicides described above to be effective to many weed species.

Examples of the formulation in which the compounds of the present invention were used are explained herein-below. In the Examples, the term "parts" means parts by weight.

EXAMPLE 5 Water dispersible powder

A mixture of the compound No. 14 of the present invention (10 parts), Zeeklite (Trade Name, manufactured by Kunimine Kogyo Co., Ltd., 87.3 parts) used as the carrier material, Neopelex (Trade Name, manufactured by Kao Atlas Co., Ltd., 1.35 parts), and Solpol 800A (Trade Name, manufactured by Toho Kogyo Co., Ltd., 1.35 parts) was pulverized to give 10% water dispersible powder.

EXAMPLE 6 Emulsifiable concentrate

A mixture of the compound No. 15 of the present invention (25 parts) and Solpol 800A (10 parts) was dissolved in 65 parts of benzene to give 25% emulsifiable concentrate.

EXAMPLE 7 Granules

A mixture of the compound No. 24 of the present invention (10 parts), 50 parts of bentonite, 35 parts of Kunilite (Trade Name, manufactured by Kokuho Kogyo Co., Ltd.) and 5 parts of Solpol 800A used as the surface-active agent was pulverized. After 10 parts of water was added, the mixture was kneaded to give a homogeneous mixture and then the mixture was extruded through sieving perforations having a diameter of 0.7 mm and dried. The product was cut off to give 10% granules having length of 1-2 mm.

The compounds of the present invention are suitable for an active ingredient of herbicides since the herbicides containing these compounds do not show any phytotoxity against many useful crops like rice, soybean, cotton and the like but have excellent herbicidal activity against various weeds. More particularly, as to the herbicidal action of the compounds of the present invention, characteristic features are that the compounds kill weeds, or inhibit the growth, or suppress the growth considerably to result in a failure of growth competition against crops.

Application amount of the compounds of the present invention is generally in the range of 10 to 1000 g/10 ares, preferably 50 to 500 g/10 ares as an active ingredient although it differs depending upon the place applied, the application time, the application methods, and weeds to be avoided.

The compounds of the present invention were found to have outstanding herbicidal activity against barnyard grass as well as many weeds such as umbrella plant, monochoria, tooth cup, bulrush and so on in the use of 50-500 g/10 ares as an active ingredient, especially under submerged paddy field condition. In addition, the compounds of the present invention are highly safe to young seedling of rice plants and no affection has been observed even in the application amount of 1000 g/10 ares as an active ingredient. Therefore, the compounds of the present invention have extremely excellent characteristics as an active ingredient of herbicides to be used for paddy field. Furthermore, the application period can be considerably extended since some of the compounds of the present invention have good herbicidal activity against barnyard grass even in a growth period (1- to 3-leaf stage). That is to say, it was shown that these compounds have high applicability as an active ingredient of soil-applied herbicides in a cultivation of transplanted rice plants at the primary to medium stage and immediately after flooding in a cultivation of dry-seeded rice.

Surprisingly, it was also shown that the herbicides containing some of the compounds of the present invention have high applicability to be used in farmland because those herbicides, when they are used as soil-applied agents after the seeding of general broadleaved crops like soybean, effectively prevent gramineous weeds such as barnyard grass, crab grass, and foxtail without any phytotoxity to crops.

The herbicidal effects of the compounds of the present invention are explained in the below-stated Examples.

EXAMPLE 8 Test for the herbicidal effects under submerged conditions (I)

Paddy field soil was charged in porcelain pots having a diameter of 9 cm, and then water was added. After the soil was tilled, weed seeds were sown on the surface of the soil and two bunches of rice plants (variety: Nihonbare) being in 2-leaf stage were transplanted in 1 cm depth. The pots were flooded to give water depth of 2 cm on the next day and predetermined amount of water dispersible powder of the compounds of the present invention, which was dispersed in 10 ml of water, was added dropwise into every pots on the surface of water for the treatment. Then they were settled in a greenhouse and received water in proper time intervals. After 3 weeks from the treatment with chemicals, the herbicidal effects as well as the influences against the rice plants were examined. Evaluation is expressed by 6 stage system, details of which are shown below. The obtained results are shown in Table 2.

    ______________________________________                                         Ex-    Phytotoxicity                                                           pression                                                                              against rice plants                                                                         Herbicidal effects                                         ______________________________________                                         5      Killed       100% Prevention                                                                (Amount of residual weeds: 0%)                             5      Considerably 80% Prevention                                                    injured      (Amount of residual weeds: 20%)                            3      Substantially                                                                               60% Prevention                                                    injured      (Amount of residual weeds: 40%)                            2      A little injured                                                                            40% Prevention                                                                 (Amount of residual weeds: 60%)                            1      Slightly injured                                                                            20% Prevention                                                                 (Amount of residual weeds: 80%)                            0      No injured   0% Prevention                                                                  (Amount of residual weeds: 100%)                           ______________________________________                                    

                                      TABLE 2                                      __________________________________________________________________________     The compounds of the                                                           present invention                                                                           Phytotoxicity                                                                         Herbicidal effect                                                 Dose  against                                                                               Barnyard                                                                            Umbrella         Tooth                                No.    (g/10 ares)                                                                          rice plant                                                                            grass                                                                               plant                                                                               Bulrush                                                                             Monochoria                                                                            cup                                  __________________________________________________________________________     13     125   0      5    5    5    5      5                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    14     125   0      5    5    5    5      5                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    15     125   0      5    5    5    5      5                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    17     125   0      5    5    4    5      4                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    18     125   0      5    5    5    5      4                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    19     125   0      5    5    0    3      2                                           250   0      5    5    1    4      3                                           500   0      5    5    1    4      3                                           1000  0      5    5    2    4      4                                    20     125   0      5    5    1    4      4                                           250   0      5    5    1    5      5                                           500   0      5    5    2    5      5                                           1000  0      5    5    3    5      5                                    23     125   0      5    5    1    5      5                                           250   0      5    5    1    5      5                                           500   0      5    5    2    5      5                                           1000  0      5    5    3    5      5                                    24     125   0      5    5    1    5      5                                           250   0      5    5    3    5      5                                           500   0      5    5    4    5      5                                           1000  0      5    5    5    5      5                                    27     125   0      5    5    3    4      4                                           250   0      5    5    3    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    28     125   0      5    5    5    5      5                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    29     125   0      5    5    4    5      5                                           250   0      5    5    4    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    30     125   0      5    5    4    5      5                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    32     125   0      5    5    2    3      4                                           250   0      5    5    2    4      5                                           500   0      5    5    3    5      5                                           1000  0      5    5    4    5      5                                    34     125   0      5    5    3    5      5                                           250   0      5    5    4    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    36     125   0      5    5    2    5      5                                           250   0      5    5    3    5      5                                           500   0      5    5    3    5      5                                           1000  0      5    5    5    5      5                                    37     125   0      5    5    1    5      5                                           250   0      5    5    2    5      5                                           500   0      5    5    2    5      5                                           1000  0      5    5    3    5      5                                    38     125   0      5    5    5    5      5                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    39     125   0      5    5    5    5      5                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    45     125   0      5    5    1    5      4                                           250   0      5    5    2    5      5                                           500   0      5    5    3    5      5                                           1000  0      5    5    3    5      5                                    47     125   0      5    5    2    4      2                                           250   0      5    5    3    5      3                                           500   0      5    5    3    5      4                                           1000  0      5    5    4    5      4                                    49     125   0      5    5    2    5      5                                           250   0      5    5    3    5      5                                           500   0      5    5    3    5      5                                           1000  0      5    5    3    5      5                                    50     125   0      5    5    4    5      5                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    51     125   0      5    5    5    5      5                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    52     125   0      5    5    1    5      5                                           250   0      5    5    1    5      5                                           500   0      5    5    2    5      5                                           1000  0      5    5    2    5      5                                    53     125   0      5    5    2    5      5                                           250   0      5    5    2    5      5                                           500   0      5    5    2    5      5                                           1000  0      5    5    3    5      5                                    54     125   0      5    5    1    5      5                                           250   0      5    5    1    5      5                                           500   0      5    5    2    5      5                                           1000  0      5    5    3    5      5                                    58     125   0      5    5    4    5      5                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    62     125   0      5    5    2    5      4                                           250   0      5    5    3    5      5                                           500   0      5    5    4    5      5                                           1000  0      5    5    4    5      5                                    63     125   0      5    5    2    5      4                                           250   0      5    5    3    5      5                                           500   0      5    5    4    5      5                                           1000  0      5    5    4    5      5                                    64     125   0      5    5    5    5      5                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    67     125   0      5    5    0    5      5                                           250   0      5    5    0    5      5                                           500   0      5    5    1    5      5                                           1000  0      5    5    1    5      5                                    72     125   0      5    5    1    5      5                                           250   0      5    5    2    5      5                                           500   0      5    5    3    5      5                                           1000  0      5    5    3    5      5                                    78     125   0      5    5    4    5      5                                           250   0      5    5    4    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    79     125   0      5    5    4    5      5                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    83     125   0      5    5    5    5      5                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    85     125   0      5    5    0    5      5                                           250   0      5    5    1    5      5                                           500   0      5    5    2    5      5                                           1000  0      5    5    2    5      5                                    87     125   0      5    5    4    5      5                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    89     125   0      5    5    2    5      5                                           250   0      5    5    3    5      5                                           500   0      5    5    4    5      5                                           1000  0      5    5    4    5      5                                    90     125   0      5    5    5    5      5                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    92     125   0      5    5    5    5      5                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    94     125   0      5    5    0    3      5                                           250   0      5    5    1    4      5                                           500   0      5    5    2    4      5                                           1000  0      5    5    2    5      5                                    96     125   0      5    5    5    4      5                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    98     125   0      4    5    4    3      5                                           250   0      5    5    4    4      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    99     125   0      5    5    4    5      4                                           250   0      5    5    4    5      4                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    101    125   0      5    5    4    4      4                                           250   0      5    5    4    4      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    102    125   0      5    5    4    4      2                                           250   0      5    5    4    4      3                                           500   0      5    5    5    5      3                                           1000  0      5    5    5    5      4                                    104    125   0      5    5    2    4      4                                           250   0      5    5    3    5      5                                           500   0      5    5    4    5      5                                           1000  0      5    5    4    5      5                                    105    125   0      0    3    2    3      2                                           250   0      1    4    3    4      3                                           500   0      2    5    4    4      4                                           1000  0      2    5    4    5      4                                    106    125   0      5    5    4    5      2                                           250   0      5    5    4    5      2                                           500   0      5    5    5    5      3                                           1000  0      5    5    5    5      3                                    108    125   0      5    5    5    5      5                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    113    125   0      5    5    5    5      4                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    117    125   0      5    5    5    5      5                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    119    125   0      5    5    5    4      2                                           250   0      5    5    5    5      3                                           500   0      5    5    5    5      4                                           1000  0      5    5    5    5      4                                    120    125   0      2    5    3    5      3                                           250   0      3    5    4    5      4                                           500   0      4    5    5    5      5                                           1000  0      4    5    5    5      5                                    122    125   0      2    5    2    4      5                                           250   0      2    5    3    5      5                                           500   0      3    5    4    5      5                                           1000  0      5    5    4    5      5                                    125    125   0      5    5    5    5      5                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    126    125   0      1    4    1    2      0                                           250   0      1    5    1    2      1                                           500   0      2    5    2    3      1                                           1000  0      2    5    2    3      2                                    127    125   0      5    5    2    5      3                                           250   0      5    5    2    5      4                                           500   0      5    5    3    5      4                                           1000  0      5    5    4    5      5                                    130    125   0      3    5    2    5      5                                           250   0      3    5    4    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    132    125   0      5    5    3    5      4                                           250   0      5    5    4    5      5                                           500   0      5    5    4    5      5                                           1000  0      5    5    5    5      5                                    137    125   0      5    5    4    5      3                                           250   0      5    5    5    5      4                                           500   0      5    5    5    5      4                                           1000  0      5    5    5    5      5                                    142    125   0      5    5    4    5      3                                           250   0      5    5    5    5      4                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    146    125   0      2    5    2    2      2                                           250   0      4    5    2    3      3                                           500   0      4    5    3    4      4                                           1000  0      5    5    4    5      5                                    149    125   0      5    5    4    4      3                                           250   0      5    5    5    5      3                                           500   0      5    5    5    5      4                                           1000  0      5    5    5    5      4                                    153    125   0      5    5    3    5      3                                           250   0      5    5    3    5      3                                           500   0      5    5    4    5      4                                           1000  0      5    5    4    5      4                                    155    125   0      4    5    4    4      3                                           250   0      5    5    5    5      3                                           500   0      5    5    5    5      4                                           1000  0      5    5    5    5      4                                    157    125   0      5    5    5    5      5                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    163    125   0      5    5    5    5      5                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    170    125   0      5    5    3    5      5                                           250   0      5    5    4    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    172    125   0      5    5    4    5      5                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    174    125   0      5    5    4    5      4                                           250   0      5    5    4    5      5                                           500   0      5    5    4    5      5                                           1000  0      5    5    4    5      5                                    175    125   0      5    5    3    5      5                                           250   0      5    5    3    5      5                                           500   0      5    5    4    5      5                                           1000  0      5    5    4    5      5                                    178    125   0      5    5    4    5      5                                           250   0      5    5    4    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    181    125   0      5    5    4    5      4                                           250   0      5    5    5    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    188    125   0      5    5    4    4      3                                           250   0      5    5    4    5      4                                           500   0      5    5    5    5      4                                           1000  0      5    5    5    5      5                                    192    125   0      5    5    1    5      2                                           250   0      5    5    1    5      3                                           500   0      5    5    2    5      3                                           1000  0      5    5    3    5      4                                    195    125   0      5    5    4    5      3                                           250   0      5    5    4    5      4                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    196    125   0      5    5    3    5      4                                           250   0      5    5    4    5      5                                           500   0      5    5    5    5      5                                           1000  0      5    5    5    5      5                                    201    125   0      2    5    3    2      2                                           250   0      4    5    4    4      2                                           500   0      5    5    5    5      3                                           1000  0      5    5    5    5      5                                    203    125   0      4    5    3    4      2                                           250   0      5    5    4    5      3                                           500   0      5    5    4    5      4                                           1000  0      5    5    5    5      5                                    Benthiocarb                                                                           125   1      5    5    2    2      3                                    (Reference                                                                            250   2      5    5    2    2      3                                    agent) 500   2      5    5    3    3      4                                           1000  3      5    5    5    4      5                                    Not treated                                                                            0    0      0    0    0    0      0                                    __________________________________________________________________________

EXAMPLE 9 Test for the herbicidal effects under submerged conditions (2)

Paddy field soil was charged in porcelain pots having a diameter of 9 cm, and then water was added. After the soil was tilled, seeds of barnyard grass were sown on the surface of the soil and two bunches of rice plants (variety: Nihonbare) being in 2-leaf stage were transplanted in 1 cm depth. The pots were flooded to give water depth of 2 cm on the next day and predetermined amount of water dispersible powder of the compounds of the present invention, which was dispersed in 10 ml of water, was added dropwise into every pots on the surface of water for the treatment before the germination of and at the time of both 1.2- and 2-leaf stages of barnyard grass. The pots were settled in a greenhouse and received water in proper time intervals. The examination was carried out after 3 weeks from the treatment with the chemicals and the results were evaluated in the similar manner as in Example 8. The results are shown in Table 3.

                                      TABLE 3                                      __________________________________________________________________________     The compounds of    Herbicidal effects                                         the present invention                                                                       Phytotoxicity                                                                         against barnyard grass                                            Dose  against        1.2-  2-                                           No.    (g/10 ares)                                                                          rice plant                                                                            Pre-emergence                                                                          Leaf stage                                                                           Leaf stage                                   __________________________________________________________________________     13     12.5  0      5       --    5                                                   25    0      5       --    5                                                   50    0      5       --    5                                                   100   0      5       --    5                                            14     12.5  0      5       --    5                                                   25    0      5       --    5                                                   50    0      5       --    5                                                   100   0      5       --    5                                            15     12.5  0      5       --    5                                                   25    0      5       --    5                                                   50    0      5       --    5                                                   100   0      5       --    5                                            18     12.5  0      5       --    5                                                   25    0      5       --    5                                                   50    0      5       --    5                                                   100   0      5       --    5                                            20     12.5  0      2       2     --                                                  25    0      3       3     --                                                  50    0      4       3     --                                                  100   0      5       4     --                                           23     12.5  0      5       4     --                                                  25    0      5       4     --                                                  50    0      5       5     --                                                  100   0      5       5     --                                           28     12.5  0      5       5     --                                                  25    0      5       5     --                                                  50    0      5       5     --                                                  100   0      5       5     --                                           34     12.5  0      5       4     --                                                  25    0      5       5     --                                                  50    0      5       5     --                                                  100   0      5       5     --                                           37     12.5  0      4       4     --                                                  25    0      5       5     --                                                  50    0      5       5     --                                                  100   0      5       5     --                                           49     12.5  0      2       1     --                                                  25    0      4       3     --                                                  50    0      5       4     --                                                  100   0      5       4     --                                           50     12.5  0      5       4     --                                                  25    0      5       5     --                                                  50    0      5       5     --                                                  100   0      5       5     --                                           51     12.5  0      5       5     --                                                  25    0      5       5     --                                                  50    0      5       5     --                                                  100   0      5       5     --                                           53     12.5  0      4       4     --                                                  25    0      5       5     --                                                  50    0      5       5     --                                                  100   0      5       5     --                                           54     12.5  0      4       4     --                                                  25    0      5       5     --                                                  50    0      5       5     --                                                  100   0      5       5     --                                           58     12.5  0      5       5     --                                                  25    0      5       5     --                                                  50    0      5       5     --                                                  100   0      5       5     --                                           78     12.5  0      4       2     --                                                  25    0      5       4     --                                                  50    0      5       5     --                                                  100   0      5       5     --                                           87     12.5  0      5       5     --                                                  25    0      5       5     --                                                  50    0      5       5     --                                                  100   0      5       5     --                                           92     12.5  0      5       5     --                                                  25    0      5       5     --                                                  50    0      5       5     --                                                  100   0      5       5     --                                           96     12.5  0      5       3     --                                                  25    0      5       3     --                                                  50    0      5       4     --                                                  100   0      5       5     --                                           101    12.5  0      5       5     --                                                  25    0      5       5     --                                                  50    0      5       5     --                                                  100   0      5       5     --                                           102    12.5  0      5       5     --                                                  25    0      5       5     --                                                  50    0      5       5     --                                                  100   0      5       5     --                                           113    12.5  0      5       5     --                                                  25    0      5       5     --                                                  50    0      5       5     --                                                  100   0      5       5     --                                           125    12.5  0      5       2     --                                                  25    0      5       2     --                                                  50    0      5       4     --                                                  100   0      5       5     --                                           Benthiocarb                                                                           12.5  0      2       1     1                                            (Reference                                                                            25    0      3       2     2                                            agent) 50    0      4         2.5   2.5                                               100   1      5       4     4                                            Not treated                                                                           0     0      0       0     0                                            __________________________________________________________________________

EXAMPLE 10 Test for the Herbicidal Effects by the Surface Treatment of Farmland Soil

Farmland soil was charged into porcelain pots having a diameter of 12 cm and several kinds of crop seeds together with weed seeds were sown. The seeds were further covered by the soil in 1 cm thickness. Predetermined amount of water dispersible powder of the compounds of the present invention, which was dispersed in 10 ml of water per every pots, was sprayed on the surface of soil for the treatment. The pots were stationarily placed in a greenhouse and received sprayed water in proper time intervals. After 3 weeks from the treatment with the chemicals, the herbicidal effects and the influences against soybean and cotton plants were examined in the similar manner as in Example 8. The results are shown in Table 4.

                                      TABLE 4                                      __________________________________________________________________________     The compounds of                                                               the present invention                                                                        Phytotoxicity                                                                            Herbicidal effects                                            Dose   Soybean                                                                             Cotton                                                                              Barnyard                                                                            Crab                                              No.    (g/10 ares)                                                                           plant                                                                               plant                                                                               grass                                                                               grass                                                                              Foxtail                                       __________________________________________________________________________     13      50    0    0    4.5  5   4.5                                                  100    0    0    5    5   5                                                    200    0    0    5    5   5                                                    400    0    0    5    5   5                                             14      50    0    0    4.5  5   4.5                                                  100    0    0    5    5   5                                                    200    0    0    5    5   5                                                    400    0    0    5    5   5                                             15      50    0    0    5    5   5                                                    100    0    0    5    5   5                                                    200    0    0    5    5   5                                                    400    0    0    5    5   5                                             18      50    0    0    4    5   4                                                    100    0    0    5    5   5                                                    200    0    0    5    5   5                                                    400    0    0    5    5   5                                             20      50    0    0    2    3   2                                                    100    0    0    3    4   4                                                    200    0    0    4    5   4                                                    400    0    0    4    5   4                                             23      50    0    0    5    5   5                                                    100    0    0    5    5   5                                                    200    0    0    5    5   5                                                    400    0    0    5    5   5                                             28      50    0    0    5    5   5                                                    100    0    0    5    5   5                                                    200    0    0    5    5   5                                                    400    0    0    5    5   5                                             34      50    0    0    4    5   4                                                    100    0    0    4    5   5                                                    200    0    0    5    5   5                                                    400    0    0    5    5   5                                             37      50    0    0    5    5   5                                                    100    0    0    5    5   5                                                    200    0    0    5    5   5                                                    400    0    0    5    5   5                                             49      50    0    0    2    3   2                                                    100    0    0    3    5   3                                                    200    0    0    4    5   3                                                    400    0    0    4    5   4                                             50      50    0    0    4    5   4                                                    100    0    0    4.5  5   5                                                    200    0    0    5    5   5                                                    400    0    0    5    5   5                                             51      50    0    0    5    5   5                                                    100    0    0    5    5   5                                                    200    0    0    5    5   5                                                    400    0    0    5    5   5                                             53       50   0    0    4    5   4                                                    100    0    0    5    5   5                                                    200    0    0    5    5   5                                                    400    0    0    5    5   5                                             54      50    0    0    4    5   4                                                    100    0    0    5    5   5                                                    200    0    0    5    5   5                                                    400    0    0    5    5   5                                             58      50    0    0    5    5   5                                                    100    0    0    5    5   5                                                    200    0    0    5    5   5                                                    400    0    0    5    5   5                                             78      50    0    0    3    4   3                                                    100    0    0    4    5   4                                                    200    0    0    5    5   4                                                    400    0    0    5    5   5                                             87      50    0    0    5    5   5                                                    100    0    0    5    5   5                                                    200    0    0    5    5   5                                                    400    0    0    5    5   5                                             92      50    0    0    5    5   5                                                    100    0    0    5    5   5                                                    200    0    0    5    5   5                                                    400    0    0    5    5   5                                             96      50    0    0    4    5   4                                                    100    0    0    5    5   5                                                    200    0    0    5    5   5                                                    400    0    0    5    5   5                                             101     50    0    0    5    5   5                                                    100    0    0    5    5   5                                                    200    0    0    5    5   5                                                    400    0    0    5    5   5                                             102     50    0    0    4    5   4                                                    100    0    0    5    5   5                                                    200    0    0    5    5   5                                                    400    0    0    5    5   5                                             113     50    0    0    4    5   4                                                    100    0    0    5    5   5                                                    200    0    0    5    5   5                                                    400    0    0    5    5   5                                             125     50    0    0    4    4   4                                                    100    0    0    4    5   4                                                    200    0    0    5    5   5                                                    400    0    0    5    5   5                                             Benthiocarb                                                                            50    0    0    3    4   3                                             (Reference                                                                            100    0    0    4    5   4                                             agent) 200    0    0    5    5   5                                                    400    0    0    5    5   5                                             Not treated                                                                            0     0    0    0    0   0                                             __________________________________________________________________________ 

What is claimed is:
 1. A carbamate compound of the formula (I) ##STR4## wherein X is 2-naphthyl, 5-indanyl, 5,6,7,8-tetrahydro-2-naphthyl, 1,4-methano-1,2,3,4-tetrahydro-6-naphthyl, 1,4-ethano-1,2,3,4-tetrahydro-6-naphthyl, or phenyl having one or more substituents which may be the same or different, and are selected from the group consisting of halogen, lower alkyl, lower alkenyl, lower alkoxy, lower alkenyloxy, lower alkynyloxy, lower alkylthio, lower alkylamino, (hydroxy)-lower alkyl, (lower alkoxy)-lower alkyl, (C₁ -C₂) acyl, nitro, cyano, methylenedioxy, and halogenated lower alkyl,Y is an oxygen atom or a sulfur atom, Z is lower alkyl, W is pyridyl substituted by one or two of the same substituents selected from the group consisting of halogen, lower alkyl, and lower alkylamino when X is 2-naphthyl but W is pyridyl which may be substituted by one or two of the same or different substituents selected from the group consisting of halogen, nitro, lower alkyl, lower alkoxy, lower alkylthio, and lower alkylamino when X is other than 2-naphthyl.
 2. The carbamate of claim 1, whereinX is 2-naphthyl, 5-indanyl, 5,6,7,8-tetrahydro-2-naphthyl, 1,4-methano-1,2,3,4-tetrahydro-6-naphthyl, 1,4-ethano-1,2,3,4-tetrahydro-6-naphthyl, or phenyl having one to three of the same or different substituents selected from the group consisting of halogen, lower alkyl, lower alkenyl, lower alkoxy, lower alkenyloxy, lower alkynyloxy, lower alkylthio, lower alkylamino, (hydroxy)-lower alkyl, (lower alkoxy)-lower alkyl, (C₁ -C₂) acyl, nitro, cyano, methylenedioxy, and halogenated lower alkyl.
 3. The carbamate of claim 2, whereinX is 2-naphthyl, 5-indanyl, 5,6,7,8-tetrahydro-2-naphthyl, 1,4-methano-1,2,3,4-tetrahydro-6-naphthyl, 1,4-ethano-1,2,3,4-tetrahydro-6-naphthyl, or phenyl having one to three of the same or different substituents selected from the group consisting of a chlorine atom, a bromine atom, alkyl of 1 to 6 carbon atoms, alkenyl of 3 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkenyloxy of 3 carbon atoms, alkynyloxy of 3 carbon atoms, methylthio, dimethylamino, hydroxymethyl, hydroxyethyl, methoxymethyl, acyl of 1 to 2 carbon atoms, nitro, cyano, methylenedioxy, trifluoromethyl, and bromoethyl.
 4. The carbamate of claim 1, whereinZ is alkyl of 1 to 3 carbon atoms.
 5. The carbamate of claim 1, whereinW is pyridyl substituted by one or two of the same substituents selected from the group consisting of a chlorine atom, alkyl of 1 to 2 carbon atoms, and dimethylamino when X is 2-naphthyl but W is pyridyl which may be substituted by one or two of the same or different substituents selected from the group consisting of a chlorine atom, a bromine atom, nitro, alkyl of 1 to 2 carbon atoms, methoxy, ethoxy, methylthio, methylamino, and dimethylamino when X is other than 2-naphthyl.
 6. The carbamate of claim 1, whereinX is 2-naphthyl, 5-indanyl, 5,6,7,8-tetrahydro-2-naphthyl, 1,4-methano-1,2,3,4-tetrahydro-6-naphthyl, 1,4-ethano-1,2,3,4-tetrahydro-6-naphthyl, or phenyl having one to three of the same or different substituents selected from the group consisting of a chlorine atom, a bromine atom, alkyl of 1 to 6 carbon atoms, alkenyl of 3 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkenyloxy of 3 carbon atoms, alkynyloxy of 3 carbon atoms, methylthio, dimethylamino, hydroxy-methyl, hydroxyethyl, methoxymethyl, acyl of 1 to 2 carbon atoms, nitro, cyano, methylenedioxy, trifluoromethyl, and bromoethyl, Y is an oxygen atom or a sulfur atom, Z is alkyl of 1 to 3 carbon atoms, W is pyridyl substitued by one or two of the same substituents selected from the group consisting of a chlorine atom, alkyl of 1 to 2 carbon atoms, and dimethylamino when X is 2-naphthyl but W is pyridyl which may be substituted by one or two of the same or different substituents selected from the group consisting of a chlorine atom, a bromine atom, nitro, alkyl of 1 to 2 carbon atoms, methoxy, ethoxy, methylthio, methylamino, and dimethylamino when X is other than 2-naphthyl.
 7. A herbicide comprisingthe carbamate of formula (I) ##STR5## as an active ingredient, and a carrier.
 8. A herbicide of claim 7 further comprising 3',4'-dichloropropionanilide.
 9. The herbicide of claim 8 wherein the carbamate is O-3-tert-butylphenyl N-(6-methoxy-2-pyridyl)-N-methylthiocarbamate. 